Herbicidal sulfonamides

ABSTRACT

Thiocarbonylsulfonylureas, useful as herbicides and plant growth regulants, herbicidal compositions employing these compounds and methods of applying them to soil or directly to plants have been discovered.

RELATED APPLICATION

This application is a divisional of copending application U.S. Ser. No. 856,781 filed May 2, 1986, now U.S. Pat. No. 4,675,045 which is a continuation-in-part of U.S. Ser. No. 740,029 filed May 31, 1985, now abandoned.

BACKGROUND OF THE INVENTION

This invention relates to sulfonylureas useful as herbicides and plant growth regulants. More particularly, it relates to o-thiocarbonylsulfonylureas having useful herbicidal and plant growth regulant activity.

U.S. Pat. No. 4,394,506 teaches herbicidal carboxylic ester sulfonylureas of the formula ##STR1## where, in part, Q is O, S or NR₆ ;

R is C₁ -C₁₂ alkyl, C₃ -C₁₀ alkenyl, C₃ -C₁₀ alkynyl, C₂ -C₆ alkyl substituted with 1-4 substituents selected from 0-3 atoms of F, Cl or Br, 0-2 methoxy groups and 0-1 cyano group; CH₂ CN; CH(R₇ ')CO₂ CH₃ or CH(R₇ ')CO₂ C₂ H₅ where R₇ ' is H or CH₃ ; C₃ -C₆ alkenyl substituted with 1-3 atoms of F, Cl or Br; etc.

R₂ is H, Cl, Br, F, C₁ -C₃ alkyl, NO₂, etc.

R₃ is H, Cl, Br, F or CH₃ ;

R₄ is H or CH₃ ;

R₅ is H, CH₃ or OCH₃ ;

R₆ is H, C₁ -C₆ alkyl, allyl, CH₂ CN or CH₂ CH₂ CN; and

R and R₆ can be taken together to form (CH₂)₄, (CH₂)₅, (CH₂)₆, CH₂ CH₂ OCH₂ CH₂ or CH₂ CH₂ N(CH₃)CH₂ CH₂.

U.S. Pat. No. 4,348,219 discloses herbicidal phenylacetic ester sulfonylureas of the formula ##STR2## wherein L is CO₂ R₁₀, CONR₃ R₄ or CN;

R is H, F, Cl, Br, NO₂, CF₃, C₁ -C₃ alkyl or C₁ -C₃ alkoxy;

R₁ is H or C₁ -C₄ alkyl;

R₂ is H or CH₃ ;

R₈ is H, CH₃ or OCH₃ ; and

W is O or S.

U.S. Pat. No. 4,420,325 covers herbicidal benzylsulfonylureas of the formula ##STR3## wherein R₁ is, inter alia, F, Cl, Br, CF₃, C₁ -C₃ alkoxy, C₁ -C₃ alkyl;

R₂ is H, Cl, Br, F, CF₃ or OCH₃ ;

R₉ is H or C₁ -C₃ alkyl;

W is O or S;

R₈ is H or CH₃ ; etc.

U.S. Pat. No. 4,481,029 teaches herbicidal sulfonylureas of Formulae I, II and III: ##STR4## wherein W' is O or S;

A' is H, Cl, Br, C₁ -C₄ alkyl, OCH₃, NO₂ or CF₃ ;

A is C(O)QR^(I) or C(T)R^(II) ;

Q is O, S or NR₆ ;

R^(I) is, inter alia, C₁ -C₆ alkyl or C₃ -C₆ alkenyl;

B is ##STR5## or ##STR6## etc.

European Patent Application No. 95,925 (published Dec. 7, 1983) discloses, in part, herbicidal sulfonylureas of the formula ##STR7## wherein Q is, inter alia, ##STR8## R is H or CH₃ ; R₁₀ is H, C₁ -C₄ alkyl, C₃ -C₄ alkenyl, etc.;

R₁₁ is H, C₁ -C₃ alkyl, F, Cl, Br, NO₂, etc.

R₁₂ is H or CH₃ ;

R₁₃ and R₁₄ are independently H, C₁ -C₃ alkyl, OR₁₆, F, Cl, Br, etc.;

R₁₅ is H or CH₃ ; etc.

U.S. Pat. No. 4,544,401 and U.S. Pat. No. 4,435,206 disclose herbicidal pyridinesulfonylureas.

The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food needs, such as soybeans, barley, wheat and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing the loss of a portion of such valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency.

A wide variety of materials, useful for killing, or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need exists, however, for still more effective herbicides that destroy or retard weeds without causing signficant damage to useful crops.

SUMMARY OF THE INVENTION

This invention relates to novel compunds of Formula I, agriculturally suitable compositions containing them, and their method-of-use as general preemergence and/or postemergence herbicides, or plant growth regulants. ##STR9## wherein J is ##STR10## W is O or S; R is H or CH₃ ;

E is a single bond or --CH₂ --;

Q is Q₁, Q₂ or Q₃ ;

Q₁ is ##STR11## Q₂ is ##STR12## Q₃ is ##STR13## n is 0 or 1; W₁ is O or S;

R₁ is H, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, Cl, Br, F, NO₂, C₁ -C₃ alkoxy, SO₂ NR_(a) R_(b), C₁ -C₃ alkylthio, C₁ -C₃ alkylsulfinyl, C₁ -C₃ alkylsulfonyl, CN, CO₂ R_(c), C₁ -C₃ haloalkoxy, C₁ -C₃ haloalkylthio, CH₂ OCH₃, CH₂ SCH₃, CH₂ CN, NH₂, NHCH₃ or N(CH₃)₂ ;

R₂ is H, Cl, Br, C₁ -C₄ alkyl, C₁ -C₃ alkoxy or C₁ -C₃ alkylthio;

R₃ is H, C₁ -C₄ alkyl, C₃ -C₄ alkenyl or phenyl;

R_(a) is H, C₁ -C₄ alkyl, C₂ -C₃ cyanoalkyl or C₁ -C₃ alkoxy;

R_(b) is H, C₁ -C₄ alkyl or C₃ -C₄ alkenyl; or

R_(a) and R_(b) may be taken together as (CH₂)₃, (CH₂)₄, (CH₂)₅ or CH₂ CH₂ OCH₂ CH₂ ;

R_(c) is C₁ -C₄ alkyl, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl, C₂ -C₄ haloalkyl, C₂ -C₃ cyanoalkyl, C₅ -C₆ cycloalkyl, C₄ -C₇ cycloalkylalkyl or C₂ -C₄ alkoxyalkyl;

R₄ is C₁ -C₁₂ alkyl, C₃ -C₁₀ alkenyl, C₃ -C₁₀ alkynyl, C₂ -C₆ alkyl substituted with 1-4 substituents selected from

(a) 0-3 atoms of F, Cl or Br,

(b) 0-2 OCH₃ groups,

(c) 0-1 C₂ -C₃ alkoxy, phenoxy, chloroethoxy or trichloroethoxy groups,

(d) 0-2 substituents selected from OH, OC(O)R₅, OC(O)OR₅, OC(O)NR₅ R₆, OP(O)(OR₇)₂, OSO₂ R₅, OSO₂ NR₅ R₆, OSi(R₈)₂ R₇ or S(O)_(m) R₅, or

(e) 0-1 cyano group, CH₂ CN, CH₂ OR₉, CH(R₁₀)CO₂ CH₃, CH(R₁₀)CO₂ C₂ H₅, C₃ -C₆ haloalkenyl, C₃ -C₆ haloalkynyl, C₅ -C₈ cycloalkyl, C₅ -C₈ cycloalkenyl, C₄ -C₁₀ cycloalkylalkyl, C₄ -C₈ cycloalkylalkyl substituted with 1-2 CH₃ groups, C₅ -C₆ cycloalkyl substituted with

(a) OCH₃,

(b) C₂ -C₄ alkyl,

(c) F, Cl or Br, or

(d) 1-4 CH₃ groups, ##STR14## R₅ is C₁ -C₄ alkyl substituted with 0-3 atoms of F, Cl or Br, 0-2 OCH₃ groups or 0-1 CN, C₃ -C₄ alkenyl substituted with 0-3 atoms of F, Cl or Br, C₃ -C₄ alkynyl or ##STR15## R₆ is H or C₁ -C₂ alkyl; R₇ is C₁ -C₄ alkyl or phenyl;

R₈ is C₁ -C₂ alkyl;

m is 0, 1 or 2;

p is 0 or 1;

W₂ is O or S;

R₉ is C₁ -C₃ alkyl, chloroethyl, trichloroethyl, phenyl, CH₂ CH₂ OCH₃, CH₂ CH₂ OC₂ H₅ or ##STR16## R₁₀ is H or CH₃ ; R₁₁ is H, C₁ -C₃ alkyl, Cl, Br, OCH₃ or OC₂ H₅ ;

R₁₂ is H, F, Cl, Br, CH₃, OCH₃, SCH₃, SO₂ CH₃, NO₂ or CF₃ ;

R₁₃ is C₁ -C₄ alkyl;

R₁₄ is C₁ -C₄ alkyl;

R₁₅ is H, C₁ -C₆ alkyl, C₂ -C₃ alkyl substituted with C₁ -C₃ alkoxy or phenoxy, C₃ -C₆ alkenyl, C₃ -C₆ alkynyl, C₃ -C₆ cycloalkyl, C₅ -C₆ cycloalkenyl, C₄ -C₇ cycloalkylalkyl, C₅ -C₆ cycloalkyl substituted with CH₃ or OCH₃, CH₂ CN, CH₂ CH₂ CN, OCH₃, OC₂ H₅, N(CH₃)₂, ##STR17## R₁₆ is H, C₁ -C₆ alkyl, CH₂ CH═CH₂, CH₂ CN or CH₂ CH₂ CN; or

R₁₅ and R₁₆ may be taken together to form (CH₂)₃, (CH₂)₄, (CH₂)₅, (CH₂)₆, CH₂ CH═CHCH₂, CH₂ CH₂ OCH₂ CH₂ or CH₂ CH₂ N(CH₃)CH₂ CH₂ ;

R₁₇ is H or CH₃ ;

R₁₈ is H, C₁ -C₃ alkyl, Cl, Br, OCH₃ or OC₂ H₅ ;

R₁₉ is H, C₁ -C₄ alkyl, OCH₃, F, Br, Cl, CF₃, CN, NO₂, SO₂ CH₃, SCH₃ or N(CH₃)₂ ; ##STR18## X is H, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄ haloalkyl, C₁ -C₄ haloalkylthio, C₁ -C₄ alkylthio, halogen C₂ -C₅ alkoxyalkoxy, amino, C₁ -C₃ alkylamino or di(C₁ -C₃)alkylamino;

Y is H, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄ haloalkylthio, C₁ -C₄ alkylthio, C₂ -C₅ alkoxyalkyl, C₂ -C₅ alkoxyalkoxy, amino, C₁ -C₃ alkylamino, di(C₁ -C₃)alkylamino, C₃ -C₄ alkenyloxy, C₃ -C₄ alkynyloxy, C₂ -C₅ alkylsulfinylalkyl, C₁ -C₄ haloalkyl, C₂ -C₅ alkylsulfonylalkyl, C₃ -C₅ cycloalkyl, C₂ -C₄ alkynyl, C₂ -C₅ alkylthioalkyl, ##STR19## or N(OCH₃)CH₃ ; W₃ and W₄ are independently O or S;

q is 2 or 3;

R_(d) is H or CH₃ ;

R_(e) is C₁ -C₂ alkyl;

R_(f) is C₁ -C₂ alkyl;

Z is CH or N;

Y₁ is O or CH₂ ;

X₁ is CH₃, OCH₃, OC₂ H₅ or OCF₂ H;

X₂ is CH₃, C₂ H₅ or CH₂ CF₃ ;

Y₂ is OCH₃, OC₂ H₅, SCH₃, SC₂ H₅, OCF₂ H, SCF₂ H, CH₃ or CH₂ CH₃ ;

X₃ is CH₃ or OCH₃ ;

Y₃ is H or CH₃ ;

Z₁ is CH or N;

X₄ is CH₃, OCH₃, OC₃ H₅, CH₂ OCH₃ or Cl; and

Y₄ is CH₃, OCH₃. OC₂ H₅ or Cl;

and their agriculturally suitable salts; provided that

(a) when W is S, then R is H, A is A-1, and Y is CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃, C₂ H₅, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, OCH₂ CH₂ OCH₃, CH(OCH₃)₂ or ##STR20## (b) when X is Cl, Br, F or I, then Z is CH and Y is OCH₃, OC₂ H₅, NH₂, NHCH₃, N(CH₃)₂ or OCF₂ H;

(c) when X or Y is C₁ haloalkoxy, then Z is CH;

(d) the total number of carbon atoms of R₄ is less than or equal to 13;

(e) the combined total number of carbon atoms of R₁₅ and R₁₆ is less than or equal to 10;

(f) when R₁₅ is CH₂ CN or CH₂ CH₂ CN, then R₁₆ is CH₂ CN or CH₂ CH₂ CN;

(g) when R₁₅ is OCH₃ or OC₂ H₅, then R₁₆ is H or CH₃ ;

(h) when R₄ is disubstituted with substituents selected from OH, OC(O)R₅, OC(O)OR₅, OC(O)NR₅ R₆, OP(O)(OR₇)₂, OSO₂ R₅, OSO₂ NR₅ R₆, OSi(R₈)₂ R₇ or S(O)_(m) R₅, then the two substituents are identical and are not on the same carbon atom, and the carbon atom bonded to W₁ does not bear any of the above substituents and must be substituted by at least one hydrogen atom;

(i) when E is CH₂, then n is 0;

(j) when the total number of carbon atoms of X and Y is greater than four, then the number of carbons of R₁ is less than or equal to two, the number of carbons of R₂ is less than or equal to two, and the nunber of carbons of Q is less than or equal to four; and

(k) X₄ and Y₄ are not simultaneously Cl.

In the above definitions, the term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl", denotes straight chain or branched alkyl, e.g. methyl, ethyl, n-propyl, isopropyl or the different butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl or dodecyl isomers.

Alkoxy denotes methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butyl isomers.

Alkenyl denotes straight chain or branched alkenes, e.g. vinyl, 1-propenyl, 2-propenyl, 3-propenyl and the different butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl or decenyl isomers.

Alkynyl denotes straight chain or branched alkynes, e.g. ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl and decynyl isomers.

Alkylsulfonyl denotes methylsulfonyl, ethylsulfonyl and the different propylsulfonyl and butylsulfonyl isomers.

Alkylthio, alkylsulfinyl, alkylamino, alkylsulfamoyl, etc. are defined in an analogous manner.

Cycloalkyl denotes, e.g. cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Cycloalkenyl means cyclopentenyl or cyclohexenyl.

The term "halogen", either alone or in compound words such as "haloalkyl", denotes fluorine, chlorine, bromine or iodine.

The total number of carbon atoms in a substituent group is indicated by the C_(i) -C_(j) prefix where i and j are numbers from 1 to 12. For example, C₁ -C₃ alkylsulfonyl would designate methylsulfonyl through propylsulfonyl, C₂ alkoxyalkoxy would designate OCH₂ OCH₃, C₂ cyanoalkyl would designate CH₂ CN and C₃ cyanoalkyl would designate CH₂ CH₂ CN and CH(CN)CH₃. The term C₄ -C₁₀ cycloalkylalkyl means cyclopropylmethyl through cyclononylmethyl or cyclopropylheptyl.

Preferred for reasons of greater ease of synthesis and/or greater herbicidal efficacy are:

(1) Compounds of Formula I where Q is Q₁.

(2) Compounds of Formula I where Q is Q₂ or Q₃.

(3) Compounds of Preferred 1 where W is O; R is H; and the carbon of R₄ bonded to W₁ is also bonded to at least one hydrogen.

(4) Compounds of Preferred 3 where

X is CH₃, OCH₃, OC₂ H₅, Cl, Br, F, I, OCF₂ H, CH₂ F, CF₃, OCH₂ CH₂ F, OCH₂ CHF₂, OCH₂ CF₃, CH₂ Cl or CH₂ Br; and

Y is H, CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃, NHCH₃, N(OCH₃)CH₃, N(CH₃)₂, C₂ H₅, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, CH₂ OC₂ H₅, OCH₂ CH₂ OCH₃, CH₂ SCH₃, CH₂ SC₅ H₅, cyclopropyl, ##STR21## OCF₂ H, SCF₂ H, C.tbd.CH or C.tbd.CCH₃. (5) Compounds of Preferred 4 where

R₄ is C₁ -C₄ alkyl, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl, C₂ -C₄ alkyl substituted with 1-3 substituents selected from 0-3 atoms of F or Cl, 0-2 OCH₃ or 0-1 CN, or C₃ -C₄ alkenyl substituted with 1-3 Cl.

(6) Compounds of Preferred 5 where

R₂ is H; and

R₁ is in the 5-position and selected from H, F, Cl, Br, C₁ -C₂ alkyl, C₁ -C₃ alkoxy or C₁ -C₃ alkylthio.

(7) Compounds of Preferred 6 where

A is A-1;

X is CH₃, OCH₃, OC₂ H₅, Cl, OCF₂ H or OCH₂ CF₃ ; and

Y is CH₃, OCH₃, C₂ H₅, CH₂ OCH₃, NHCH₃ or CH(OCH₃)₂.

(8) Compounds of Preferred 7 where

R₁ is H, Cl, CH₃ or OCH₃ ;

n is 0; and

E is a single bond.

(9) Compounds of Preferred 8 where

R₄ is C₁ -C₃ alkyl, CH₂ CH═CH₂, CH₂ C.tbd.CH, CH₂ CH₂ Cl or CH₂ CH₂ OCH₃.

(10) Compounds of Preferred 9 where

Q is --C(S)W₁ R₄ ; and

W₁ is S.

(11) Compounds of Preferred 9 where

Q is --C(S)W₁ R₄ ; and

W₁ is O.

(12) Compounds of Preferred 10 where J is J-1.

(13) Compounds of Preferred 10 where J is J-2.

(14) Compounds of Preferred 10 where J is J-3.

(15) Compounds of Preferred 10 where J is J-4.

(16) Compounds of Preferred 10 where J is J-5.

(17) Compounds of Preferred 10 where J is J-6.

(18) Compounds of Preferred 10 where J is J-7.

(19) Compounds of Preferred 10 where J is J-8.

(20) Compounds of Preferred 10 where J is J-9.

(21) Compounds of Preferred 10 where J is J-10.

(22) Compounds of Preferred 10 where J is J-11.

(23) Compounds of Preferred 10 where J is J-12.

(24) Compounds of Preferred 11 where J is J-1.

(25) Compounds of Preferred 11 where J is J-2.

(26) Compounds of Preferred 11 where J is J-3.

(27) Compounds of Preferred 11 where J is J-4.

(28) Compounds of Preferred 11 where J is J-5.

(29) Compounds of Preferred 11 where J is J-6.

(30) Compounds of Preferred 11 where J is J-7.

(31) Compounds of Preferred 11 where J is J-8.

(32) Compounds of Preferred 11 where J is J-9.

(33) Compounds of Preferred 11 where J is J-10.

(34) Compounds of Preferred 11 where J is J-11.

(35) Compounds of Preferred 11 where J is J-12.

(36) Compounds of Preferred 2 where

W is O;

R is H; and

R₁₄ is other than C(CH₃)₃.

(37) Compounds of Preferred 36 where

X is CH₃, OCH₃, OC₂ H₅, Cl, Br, F, I, OCF₂ H, CH₂ F, CF₃, OCH₂ CH₂ F, OCH₂ CHF₂, OCH₂ CF₃, CH₂ Cl or CH₂ Br; and

Y is H, CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃, NHCH₃, N(OCH₃)CH₃, N(CH₃)₂, C₂ H₅, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, CH₂ OC₂ H₅, OCH₂ CH₂ OCH₃, CH₂ SCH₃, CH₂ SC₂ H₅, cyclopropyl, ##STR22## OCF₂ H, SCF₂ H, C.tbd.CH or C.tbd.CCH₃. (38) Compounds of Preferred 37 where

R₁₅ is H, C₁ -C₃ alkyl, C₃ -C₄ alkenyl or C₃ -C₄ alkynyl;

R₁₆ is H, C₁ -C₃ alkyl or CH₂ CH═CH₂ ; or

R₁₅ and R₁₆ are taken together to form (CH₂)₄, (CH₂)₅ or CH₂ CH₂ OCH₂ CH₂.

(39) Compounds of Preferred 38 where

R₂ is H; and

R₁ is in the 5-position and selected from H, F, Cl, Br, C₁ -C₂ alkyl, C₁ -C₃ alkoxy or C₁ -C₃ alkylthio.

(40) Compounds of Preferred 39 where

A is A-1;

X is CH₃, OCH₃, OC₂ H₅, Cl, OCF₂ H or OCH₂ CF₃ ; and

Y is CH₃, OCH₃, C₂ H₅, CH₂ OCH₃, NHCH₃ or CH(OCH₃)₂.

(41) Compounds of Preferred 40 where

R₁ is H, Cl, CH₃ or OCH₃ ;

n is 0; and

E is a single bond.

(42) Compounds of Preferred 41 where

R₁₃ is C₁ -C₂ alkyl;

R₁₄ is C₁ -C₂ alkyl;

R₁₅ is H or C₁ -C₃ alkyl; and

R₁₆ is H or C₁ -C₃ alkyl.

(43) Compounds of Preferred 42 where

Q is --C(S)NR₁₅ R₁₆.

(44) Compounds of Preferred 42 where

Q is --C(═NR₁₃)W₁ R₁₄.

(45) Compounds of Preferred 43 where J is J-1.

(46) Compounds of Preferred 43 where J is J-2.

(47) Compounds of Preferred 43 where J is J-3.

(48) Compounds of Preferred 43 where J is J-4.

(49) Compounds of Preferred 43 where J is J-5.

(50) Compounds of Preferred 43 where J is J-6.

(51) Compounds of Preferred 43 where J is J-7.

(52) Compounds of Preferred 43 where J is J-8.

(53) Compounds of Preferred 43 where J is J-9.

(54) Compounds of Preferred 43 where J is J-10.

(55) Compounds of Preferred 43 where J is J-11.

(56) Compounds of Preferred 43 where J is J-12.

(57) Compounds of Preferred 44 where J is J-1.

(58) Compounds of Preferred 44 where J is J-2.

(59) Compounds of Preferred 44 where J is J-3.

(60) Compounds of Preferred 44 where J is J-4.

(61) Compounds of Preferred 44 where J is J-5.

(62) Compounds of Preferred 44 where J is J-6.

(63) Compounds of Preferred 44 where J is J-7.

(64) Compounds of Preferred 44 where J is J-8.

(65) Compounds of Preferred 44 where J is J-9.

(66) Compounds of Preferred 44 where J is J-10.

(67) Compounds of Preferred 44 where J is J-11.

(68) Compounds of Preferred 44 where J is J-12.

Specifically preferred for reasons of their highest herbicidal activity, greatest plant growth regulant activity and/or most favorable ease of synthesis are:

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(1-pyrrolidinylthioxomethyl)benzenesulfonamide, m.p. 184° C.; and

2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N,N-dimethylbenzenecarbothioamide, m.p. 191° C.(d).

DETAILED DESCRIPTION OF THE INVENTION

Compounds of Formula I can be prepared by one or more of the methods shown below.

Equation 1 ##STR23## X=H, Si(CH₃)₂ (t-C₄ H₉)

When X is H, the methods described in U.S. Pat. No. 4,443,245 are employed. Where X is Si(CH₃)₂ (t-C₄ H₉), one equivalent of a source of fluoride ion, such as tetrabutylammonium fluoride, is used to promote the reaction.

Equation 2 ##STR24##

The reaction of Equation 2 is described in U.S. Pat. No. 4,398,939.

Compounds of Formula 1, where J is as previously described and Q contains the dithioester group can be prepared from the corresponding carboxylic acids by treatment with certain O/S exchange reagents as described by M. Yokoyama, Y. Hasegawa, H. Katanaka, Y. Kawazoe, and T. Imamoto, Synthesis 827 (1984), and U. Pedersen, B. Yde, N. M. Yousif and S.-O. Lawesson, Sulfur Letters 2, 167 (1983). An example of this reaction is shown in Equation 3.

Equation 3 ##STR25##

Compounds of Formula 1 where J is as previously described and Q contains the thioamide group can be prepared by reaction of the corresponding carboxamide with certain O/S exchange reagents described by B. Yde, N. M. Yousif, U. Pedersen, I. Thomsen, and S.-O. Lawesson, Tetrahedron, 40, 2047 (1984).

Alternatively, the thioamide group can be prepared by following the metallation procedure of Equation 4 and quenching the organometallic with an aryl or alkyl isothiocyanate.

Equation 4 ##STR26##

Compounds of Formula 1 where J is as previously described and Q contains the thionoester group can be prepared by reaction of the corresponding ester with certain O/S exchange reagents described by R. S. Pedersen, S. Scheibye, K. Clausen, and S.-O. Lawesson, Bull. Soc. Chim. Belg. 87, 293 (1978).

Compounds of Formula 1 where J is as previously described and Q is Q₃ can be prepared by metallation of the corresponding sulfonamide derivative, quenching the organometallic with a C₁ -C₄ alkyl (isocyanate or) isothiocyanate and reaction of the anionic intermediate with a C₁ -C₄ alkylating agent as shown in Equation 5.

Equation 5 ##STR27##

Agriculturally suitable salts of compounds of Formula I are also useful herbicides and can be prepared in a number of ways known to the art. For example, metal salts can be made by contacting compounds of Formula I with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion (e.g., hydroxide, alkoxide or carbonate). Quaternary amine salts can be made by similar techniques.

Salts of compounds of Formula I can also be prepared by exchange of one cation for another. Cationic exchange can be effected by direct contact of an aqueous solution of a salt of a compound of Formula I (e.g., alkali or quaternary amine salt) with a solution containing the cation to be exchanged. This method is most effective when the desired salt containing the exchanged cation is insoluble in water and can be separated by filtration.

Exchange may also be effected by passing an aqueous solution of a salt of a compound of Formula I (e.g., an alkali metal or quaternary amine salt) through a column packed with a cation exchange resin containing the cation to be exchanged for that of the original salt and the desired product is eluted from the column. This method is particularly useful when the desired salt is water-soluble.

Acid addition salts, useful in this invention, can be obtained by reacting a compound of Formula I with a suitable acid, e.g., p-toluenesulfonic acid, trichloroacetic acid or the like.

The preparation of the compounds of this invention is further illustrated by the following examples.

EXAMPLE 1 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-[(2,5-dihydro-1H-pyrrol-1-yl)thioxocarbonyl]benzenesulfonamide

To a solution of 2-[(1-pyrrolidinyl)thioxomethyl]benzenesulfonamide (0.7 g) and phenyl 4,6-(dimethoxypyrimidin-2-yl)carbamate (0.78 g) in acetonitrile (50 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (0.42 mL). After the mixture had been stirred for 18 hours at ambient temperature, an addition of water was made (100 mL) followed by acetic acid (1 mL). The precipitate was filtered and dried. The crude product (1.09 g) was recrystallized from ether (0.86 g,

m.p. 184° C. 73.5% yield).

IR: 3400 cm⁻¹, 3300 cm⁻¹, 1700 cm⁻¹.

NMR: 2.0 ppm, m, 4H; 3.3 ppm, m, 1H; 3.4 ppm, m, 1H; 3.7 ppm, m, 1H; 3.8 ppm, m, 1H; 3.9, s, 6H; 5.8 ppm, s, 1H; 7.2 ppm, dxd, 1H; 7.5 ppm, m, 2H; 8.3 ppm, d, 1H.

EXAMPLE 2 2-[(1-Pyrrolidinyl)thioxomethyl]benzenesulfonamide

To a solution of 2-(1-pyrrolidinyl)carbonylbenzenesulfonamide (5.0 g) in 1,2-dimethoxyethane (100 mL) was added 2,4-bis(4'-methoxyphenyl)-1,3,2,4-dithiaphosphetane 2,4-disulfide (Lawesson's Reagent). The slurry was heated for reflux for 2 hours under a nitrogen atmosphere. Flash chromatography of the reaction mixture on silica gel (hexane:ethyl acetate, 2:1) gave the purified product (1.88 g, m.p. 186°-7° C.);

IR: 3200 cm⁻¹, 3100 cm⁻¹.

NMR (CDCl₃): 2.0 ppm, m, 4H; 3.3 ppm, t, 2H; 3.9 ppm, t, 2H; 6.7 ppm, s, 2H; 7.3 ppm, dxd, 1H; 7.5 ppm, m, 2H; 8.0 ppm, dxd, 1H.

EXAMPLE 3 N-[(Dimethyl)(1,1-dimethylethyl)silyl]-2-[(1-methylamino)thioxomethyl]benzenesulfonamide

To a solution of N-[(dimethyl)(1,1-dimethylethyl)silyl]benzenesulfonamide (13.57 g) in dimethoxyethane (100 mL) at -78° C. was added dropwise n-butyl lithium (1.6M, 68.75 mL). The resulting solution was stirred at -20° C. for 30 minutes and then recooled to -78° C. and treated with a solution of methylisothiocyanate (5.13 mL) in dimethoxyethane (6 mL). The resulting solution was stirred at -40° C. for 4 hours. Isolation was by aqueous work-up and purification by flash chromatography (30% ethyl acetate, 70% hexane) to yield 4.65 g of product.

NMR: 10.7 ppm, bs, 1H; 7.85 ppm, d, 1H; 7.58 ppm, m, 2H; 7.28 ppm, d, 1H; 6.87 ppm, s, 1H; 3.1 ppm, d, 3H; 0.85 ppm, s, 9H; 0.13 ppm, s, 6H.

EXAMPLE 4 2-[((4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl)aminosulfonyl]benzenecarboximidothioic acid, N,S-diethylester

To a solution of phenyl 4,6-(dimethoxypyrimidin-2-yl)carbamate (0.71 g) and N-[(dimethyl)(1,1-dimethylethyl)silyl]-2-[N,S-diethylcarboximidothioate) (1.0 g) in acetonitrile (25 mL) was added to tetra-n-butylammonium fluoride trihydrate (0.82 g). After the mixture had been stirred for one hour at 25° C., aqueous work-up and purification by chromatography gave 0.34 g of product: m.p. 165°-167° C.

IR (Nujol) 1710 cm⁻¹.

NMR: 12.75 ppm, bs, 1H; 12.4 ppm, bs, 1H; 8.38 ppm, dxd, 1H; 7.6 ppm, m, 2H; 7.2 ppm, d, 1H; 5.78 ppm, s, 1H; 3.93 ppm, s, 6H; 3.4 ppm, m, 2H; 2.5 ppm, q, 2H; 1.13 ppm, dxt, 6H.

EXAMPLE 5 N-[(Dimethyl)(1,1-dimethylethyl)silyl]-2-[N,S-diethylcarboximidothioate]benzenesulfonamide

To a solution of N-[(dimethyl)(1,1-dimethylethyl)silyl]benzenesulfonamide (13.57 g) in dimethoxyethane at -78° C. was added dropwise a solution of n-butyllithium (1.6M, 70.9 mL) in dimethoxyethane (100 mL). The reaction was stirred at -30° C. for 30 minutes and recooled to -78° C. and treated dropwise with a solution of ethyl isothiocyanate (6.56 mL) in dimethoxyethane (15 mL). The reaction was stirred at -30° C. for 4 hours and recooled to -78° C. and treated with a solution of ethyl iodide (6 mL) in dimethoxyethane (15 mL). The reaction was allowed to warm to 25° C. and stir for 18 hours. Aqueous work-up and purification by flash chromatography (10% ethyl acetate, 90% hexane) gave 8.3 g of the oily product.

NMR: 8.01 ppm, d, 1H; 7.52 ppm, m, 3H; 6.25 ppm, bs, 1H; 3.65 ppm, q, 2H; 2.5 ppm, q, 2H; 1.37 ppm, t, 3H; 1.13 ppm, t, 3H; 0.90 ppm, s, 9H; 0.195 ppm, s, 6H.

By applying the procedures described above, one skilled in the art can prepare the compounds listed in Tables I-XIII.

                                      TABLE I                                      __________________________________________________________________________      ##STR28##                                                                     n R  R.sub.1                                                                              W W.sub.1                                                                           E    R.sub.4  X      Y        m.p. (°C.)                __________________________________________________________________________     0 H  H     O S  --   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                  0 H  H     O S  --   CH.sub.3 CH.sub.3                                                                              OCH.sub.3                                 0 H  H     O S  --   CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O S  --   CH.sub.3 Cl     OCH.sub.3                                 0 H  H     O S  --   CH.sub.3 CH.sub.3                                                                              OCH.sub.2 CHCH.sub.2                      0 H  H     O S  --   CH.sub.3 OCF.sub.2 H                                                                           CH.sub.3                                  0 H  H     O S  --   CH.sub.3 OCH.sub.2 OCH.sub.3                                                                   CH.sub.3                                  0 H  H     O S  --   CH.sub.3 OCH.sub.3                                                                             N(CH.sub.3).sub.2                         0 H  H     O S  --   CH.sub.3 CH.sub.3                                                                              CH(OCH.sub.3).sub.2                       0 H  H     O S  --   CH.sub.3 OC.sub.2 H.sub.5                                                                      CH.sub.3                                  0 H  H     O S  --   CH.sub.3 OCH.sub.3                                                                             NHCH.sub.3                                0 H  H     O S  --   CH.sub.3 CH.sub.3                                                                              SCH.sub.3                                 0 H  H     O S  --   CH.sub.3 CH.sub.3                                                                              CCH                                       0 H  H     O S  --   CH.sub.3 CH.sub.3                                                                              CHSCH.sub.3                               0 H  H     O S  --   CH.sub.3 CH.sub.3                                                                              SCF.sub.2 H                               0 H  H     O S  --   CH.sub.3 OCH.sub.3                                                                             N(OCH.sub.3)CH.sub.3                      0 H  H     O S  --   CH.sub.3 CH.sub.3                                                                              OCH.sub.2 CCH                             0 H  5-Cl  O S  --   CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 0 H  5-OCH.sub.3                                                                          O S  --   CH.sub.3 OCH.sub.3                                                                             OCH.sub. 3                                0 H  5-SCH.sub.3                                                                          O S  --   CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 0 CH.sub.3                                                                          H     O S  --   CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     S S  --   CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O S  CH.sub.2                                                                            CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O S  --   CH.sub.2 CHCH.sub.2                                                                     CH.sub.3                                                                              OCH.sub.3                                 0 H  H     O S  --   CH.sub.2 CHCH.sub.2                                                                     OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O S  --   CH.sub.2 C.sub.6 H.sub.5                                                                CH.sub.3                                                                              OCH.sub.3                                 0 H  5-NH.sub.2                                                                           O S  --   CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 0 H  5-NHCH.sub.3                                                                         O S       CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 0 H  5-N(CH.sub.3).sub.2                                                                  O S       CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O S  --   CH.sub.2 C.sub.6 H.sub.5                                                                OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O S  --   C.sub.6 H.sub.5                                                                         CH.sub.3                                                                              OCH.sub.3                                 0 H  H     O S  --   C.sub.6 H.sub.5                                                                         OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O S  --   p-ClC.sub.6 H.sub.5                                                                     CH.sub.3                                                                              OCH.sub.3                                 0 H  H     O S  --   p-ClC.sub.6 H.sub.5                                                                     OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O S  --   CH.sub.2 OCH.sub.3                                                                      OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O S  --   CH.sub.2 CH.sub.2 CN                                                                    OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O S  --   CH.sub.2 CCH                                                                            OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O O  --   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                  0 H  H     O O  --   CH.sub.3 CH.sub.3                                                                              OCH.sub.3                                 0 H  H     O O  --   CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O O  --   CH.sub.3 Cl     OCH.sub.3                                 0 H  H     O O  --   CH(CH.sub.3).sub.2                                                                      OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O O  --   CH.sub.2 CH.sub.2 OCH.sub.3                                                             OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O O  --   C.sub.6 H.sub.5                                                                         OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O O  --   C.sub.2 H.sub.5                                                                         OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O O  --   CH.sub.2 C.sub.6 H.sub.5                                                                OCH.sub.3                                                                             OCH.sub.3                                 0 H  5-Cl  O O  --   CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 0 H  5-OCH.sub.3                                                                          O O  --   CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 0 H  5-SCH.sub.3                                                                          O O  --   CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 0 CH.sub.3                                                                          H     O O  --   CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     S O  --   CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O O  CH.sub.2                                                                            CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 1 H  H     O S  --   CH.sub.3 CH.sub.3                                                                              OCH.sub.3                                 1 H  H     O S  --   CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 1 H  H     O S  --   CH.sub.3 Cl     OCH.sub.3                                 __________________________________________________________________________

                                      TABLE II                                     __________________________________________________________________________      ##STR29##                                                                     n R  R.sub.1                                                                              W E    R.sub.15                                                                           R.sub.16 X      Y        m.p. (°C.)               __________________________________________________________________________     0 H  H     O --   CH.sub.3                                                                           CH.sub.3 CH.sub.3                                                                              CH.sub.3                                 0 H  H     O --   CH.sub.3                                                                           CH.sub.3 CH.sub.3                                                                              OCH.sub.3                                0 H  H     O --   CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                                                               191                             0 H  H     O --   CH.sub.3                                                                           CH.sub.3 Cl     OCH.sub.3                                0 H  H     O --   (CH.sub.2).sub.4                                                                            CH.sub.3                                                                              CH.sub.3                                 0 H  H     O --   (CH.sub.2).sub.4                                                                            OCH.sub.3                                                                             CH.sub.3                                 0 H  H     O --   (CH.sub.2).sub.4                                                                            OCH.sub.3                                                                             OCH.sub.3                                                                               184                             0 H  H     O --   (CH.sub.2).sub.4                                                                            Cl     OCH.sub.3                                0 H  H     O --   H   H        CH.sub.3                                                                              CH.sub.3                                 0 H  H     O --   H   H        CH.sub.3                                                                              OCH.sub.3                                0 H  H     O --   H   H        OCH.sub.3                                                                             OCH.sub.3                                0 H  H     O --   H   H        Cl     OCH.sub.3                                0 H  H     O --   H   CH.sub.3 Cl     OCH.sub.3                                                                               239-242                         0 H  H     O --   H   CH.sub.3 CH.sub.3                                                                              CH.sub.3 177-179                         0 H  H     O --   H   CH.sub.3 CH.sub.3                                                                              OCH.sub.3                                                                               188-190                         0 H  H     O --   H   CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                                                               173-175                         0 H  H     O --   H   CH.sub.2 CHCH.sub.2                                                                     OCH.sub.3                                                                             OCH.sub.3                                0 H  H     O --   H   C.sub.6 H.sub.5                                                                         OCH.sub.3                                                                             OCH.sub.3                                0 H  H     O --   H   p-ClC.sub.6 H.sub.4                                                                     OCH.sub.3                                                                             OCH.sub.3                                0 H  H     O --   H   p-CH.sub.3 OC.sub.6 H.sub.4                                                             OCH.sub.3                                                                             OCH.sub.3                                0 H  H     O --   (CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2)                                                      CH.sub.3                                                                              CH.sub.3                                 0 H  H     O --   (CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2)                                                      CH.sub.3                                                                              OCH.sub.3                                0 H  H     O --   (CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2)                                                      OCH.sub.3                                                                             OCH.sub.3                                0 H  H     O --   H   CH(CH.sub.3).sub.2                                                                      OCH.sub.3                                                                             OCH.sub.3                                0 H  H     O --   H   C(CH.sub.3).sub.3                                                                       OCH.sub.3                                                                             OCH.sub.3                                0 H  H     O --   CH.sub.3                                                                           CH.sub.3 CH.sub.3                                                                              OCH.sub.2 CHCH.sub.2                     0 H  H     O --   CH.sub.3                                                                           CH.sub.3 OCF.sub.2 H                                                                           CH.sub.3                                 0 H  5-NH.sub.2                                                                           O --   CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                0 H  5-NHCH.sub.3                                                                         O --   CH.sub.3                                                                           CH.sub.3 OCH.sub. 3                                                                            OCH.sub.3                                0 H  5-N(CH.sub.3).sub.2                                                                  O --   CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                0 H  H     O --   CH.sub.3                                                                           CH.sub.3 OCH.sub.2 OCH.sub.3                                                                   CH.sub.3                                 0 H  H     O --   CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             N(CH.sub.3).sub.2                        0 H  H     O --   CH.sub.3                                                                           CH.sub.3 CH.sub.3                                                                              CH(OCH.sub.3).sub.2                      0 H  H     O --   CH.sub.3                                                                           CH.sub.3 OC.sub.2 H.sub.5                                                                      CH.sub.3                                 0 H  H     O --   CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             NHCH.sub.3                               0 H  H     O --   CH.sub.3                                                                           CH.sub.3 CH.sub.3                                                                              SCH.sub.3                                0 H  H     O --   CH.sub.3                                                                           CH.sub.3 CH.sub.3                                                                              CCH                                      0 H  H     O --   CH.sub.3                                                                           CH.sub.3 CH.sub.3                                                                              CH.sub.2 SCH.sub.3                       0 H  H     O --   CH.sub.3                                                                           CH.sub.3 CH.sub.3                                                                              SCF.sub.2 H                              0 H  H     O --   CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             N(OCH.sub.3)CH.sub.3                     0 H  H     O --   CH.sub.3                                                                           CH.sub.3 CH.sub.3                                                                              OCH.sub.2 C CH                           0 CH.sub.3                                                                          H     O --   CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                0 H  5-Cl  O --   CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                0 H  5-OCH.sub.3                                                                          O --   CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                0 H  5-SCH.sub.3                                                                          O --   CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                0 H  H     S --   CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                0 H  H     O CH.sub.2                                                                            CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                0 H  H     O --   CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                1 H  H     O --   CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                1 H  H     O --   CH.sub.3                                                                           CH.sub.3 CH.sub.3                                                                              OCH.sub.3                                1 H  H     O --   CH.sub.3                                                                           CH.sub.3 CH.sub.3                                                                              CH.sub.3                                 1 H  H     O --   CH.sub.3                                                                           CH.sub.3 Cl     OCH.sub.3                                0 H  H     O --   H   CH.sub.2 CH.sub.3                                                                       OCH.sub.3                                                                             OCH.sub.3                                                                               169-171                         0 H  H     O --   H   CH.sub.2 CH.sub.3                                                                       CH.sub.3                                                                              CH.sub.3 >208                            0 H  H     O --   H   CH.sub.2 CH.sub.3                                                                       CH.sub.3                                                                              OCH.sub.3                                                                               167-169                         0 H  H     O --   H   CH.sub.2 CH.sub.3                                                                       Cl     OCH.sub.3                                                                               204-206                         0 H  H     O --   H   (CH.sub.2).sub.3 OCH.sub.3                                                              CH.sub.3                                                                              CH.sub.3 144-146                         0 H  H     O --   H   (CH.sub.2).sub.3 OCH.sub.3                                                              OCH.sub.3                                                                             OCH.sub.3                                                                               155-157                         0 H  H     O --   H   (CH.sub.2).sub.3 OCH.sub.3                                                              Cl     OCH.sub.3                                                                               149-151                         __________________________________________________________________________

                                      TABLE III                                    __________________________________________________________________________      ##STR30##                                                                     n R  R.sub.1                                                                              W W.sub.1                                                                           E    R.sub.4  X      Y        m.p. (°C.)                __________________________________________________________________________     0 H  H     O S  --   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                  0 H  H     O S  --   CH.sub.3 CH.sub.3                                                                              OCH.sub.3                                 0 H  H     O S  --   CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O S  --   CH.sub.3 Cl     OCH.sub.3                                 0 H  H     O S  --   CH.sub.3 CH.sub.3                                                                              OCH.sub.2 CHCH.sub.2                      0 H  H     O S  --   CH.sub.3 OCF.sub.2 H                                                                           CH.sub.3                                  0 H  H     O S  --   CH.sub.3 OCH.sub.2 OCH.sub.3                                                                   CH.sub.3                                  0 H  H     O S  --   CH.sub.3 OCH.sub.3                                                                             N(CH.sub.3).sub.2                         0 H  H     O S  --   CH.sub.3 CH.sub.3                                                                              CH(OCH.sub.3).sub.2                       0 H  H     O S  --   CH.sub.3 OC.sub.2 H.sub.5                                                                      CH.sub.3                                  0 H  H     O S  --   CH.sub.3 OCH.sub.3                                                                             NHCH.sub.3                                0 H  H     O S  --   CH.sub.3 CH.sub.3                                                                              SCH.sub.3                                 0 H  H     O S  --   CH.sub.3 CH.sub.3                                                                              CCH                                       0 H  H     O S  --   CH.sub.3 CH.sub.3                                                                              CHSCH.sub.3                               0 H  H     O S  --   CH.sub.3 CH.sub.3                                                                              SCF.sub.2 H                               0 H  H     O S  --   CH.sub.3 OCH.sub.3                                                                             N(OCH.sub.3)CH.sub.3                      0 H  H     O S  --   CH.sub.3 CH.sub.3                                                                              OCH.sub.2 CCH                             0 H  5-Cl  O S  --   CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 0 H  5-OCH.sub.3                                                                          O S  --   CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 0 H  5-SCH.sub.3                                                                          O S  --   CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 0 CH.sub.3                                                                          H     O S  --   CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     S S  --   CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O S  CH.sub.2                                                                            CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O S  --   CH.sub.2 CHCH.sub.2                                                                     CH.sub.3                                                                              OCH.sub.3                                 0 H  H     O S  --   CH.sub.2 CHCH.sub.2                                                                     OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O S  --   CH.sub.2 C.sub.6 H.sub.5                                                                CH.sub.3                                                                              OCH.sub.3                                 0 H  5-NH.sub.2                                                                           O S  --   CH.sub.3 CH.sub.3                                                                              OCH.sub.3                                 0 H  5-NHCH.sub.3                                                                         O S  --   CH.sub.3 CH.sub.3                                                                              OCH.sub.3                                 0 H  5-N(CH.sub.3).sub.2                                                                  O S  --   CH.sub.3 CH.sub.3                                                                              OCH.sub.3                                 0 H  H     O S  --   CH.sub.2 C.sub.6 H.sub.5                                                                OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O S  --   C.sub.6 H.sub.5                                                                         CH.sub.3                                                                              OCH.sub.3                                 0 H  H     O S  --   C.sub. 6 H.sub.5                                                                        OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O S  --   p-ClC.sub.6 H.sub.4                                                                     CH.sub.3                                                                              OCH.sub.3                                 0 H  H     O S  --   p-ClC.sub.6 H.sub.4                                                                     OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O S  --   CH.sub.2 OCH.sub.3                                                                      OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O S  --   CH.sub.2 CH.sub.2 CN                                                                    OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O S  --   CH.sub.2 CCH                                                                            OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O O  --   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                  0 H  H     O O  --   CH.sub.3 CH.sub.3                                                                              OCH.sub.3                                 0 H  H     O O  --   CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O O  --   CH.sub.3 Cl     OCH.sub.3                                 0 H  H     O O  --   CH(CH.sub.3).sub.2                                                                      OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O O  --   CH.sub.2 CH.sub.2 OCH.sub.3                                                             OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O O  --   C.sub.6 H.sub.5                                                                         OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O O  --   C.sub.2 H.sub. 5                                                                        OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O O  --   CH.sub.2 C.sub.6 H.sub.5                                                                OCH.sub.3                                                                             OCH.sub.3                                 0 H  5-Cl  O O  --   CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 0 H  5-OCH.sub.3                                                                          O O  --   CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 0 H  5-SCH.sub.3                                                                          O O  --   CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 0 CH.sub.3                                                                          H     O O  --   CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     S O  --   CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 0 H  H     O O  CH.sub.2                                                                            CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 1 H  H     O S  --   CH.sub.3 CH.sub.3                                                                              OCH.sub.3                                 1 H  H     O S  --   CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                 1 H  H     O S  --   CH.sub.3 Cl     OCH.sub.3                                 __________________________________________________________________________

                                      TABLE IV                                     __________________________________________________________________________      ##STR31##                                                                     n R  R.sub.1                                                                              W E    R.sub.15                                                                           R.sub.16 X      Y        m.p. (°C.)               __________________________________________________________________________     0 H  H     O --   CH.sub.3                                                                           CH.sub.3 CH.sub.3                                                                              CH.sub.3                                 0 H  H     O --   CH.sub.3                                                                           CH.sub.3 CH.sub.3                                                                              OCH.sub.3                                0 H  H     O --   CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                0 H  H     O --   CH.sub.3                                                                           CH.sub.3 Cl     OCH.sub.3                                0 H  H     O --   (CH.sub.2 ).sub.4                                                                           CH.sub.3                                                                              CH.sub.3                                 0 H  H     O --   (CH.sub.2).sub.4                                                                            OCH.sub.3                                                                             CH.sub.3                                 0 H  H     O --   (CH.sub.2).sub.4                                                                            OCH.sub.3                                                                             OCH.sub.3                                                                               153-155                         0 H  H     O --   (CH.sub.2).sub.4                                                                            Cl     OCH.sub.3                                0 H  H     O --   H   H        CH.sub.3                                                                              CH.sub.3                                 0 H  H     O --   H   H        CH.sub.3                                                                              OCH.sub.3                                0 H  H     O --   H   H        OCH.sub.3                                                                             OCH.sub.3                                0 H  H     O --   H   H        Cl     OCH.sub.3                                0 H  H     O --   H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                 0 H  H     O --   H   CH.sub.3 CH.sub.3                                                                              OCH.sub.3                                0 H  H     O --   H   CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                                                               168-170                         0 H  H     O --   H   CH.sub.2 CHCH.sub.2                                                                     OCH.sub.3                                                                             OCH.sub.3                                0 H  H     O --   H   C.sub.6 H.sub.5                                                                         OCH.sub.3                                                                             OCH.sub.3                                0 H  H     O --   H   p-ClC.sub.6 H.sub. 4                                                                    OCH.sub.3                                                                             OCH.sub.3                                0 H  H     O --   H   p-CH.sub.3 OC.sub.6 H.sub.4                                                             OCH.sub.3                                                                             OCH.sub.3                                0 H  H     O --   (CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2)                                                      CH.sub.3                                                                              CH.sub.3                                 0 H  H     O --   (CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2)                                                      CH.sub.3                                                                              OCH.sub.3                                0 H  H     O --   (CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2)                                                      OCH.sub.3                                                                             OCH.sub.3                                0 H  H     O --   H   CH(CH.sub.3).sub.2                                                                      OCH.sub.3                                                                             OCH.sub.3                                0 H  H     O --   H   C(CH.sub.3).sub.3                                                                       OCH.sub.3                                                                             OCH.sub.3                                0 H  H     O --   CH.sub.3                                                                           CH.sub.3 CH.sub.3                                                                              OCH.sub.2 CHCH.sub.2                     0 H  H     O --   CH.sub.3                                                                           CH.sub.3 OCF.sub.2 H                                                                           CH.sub.3                                 0 H  5-NH.sub.2                                                                           O --   CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                0 H  5-NHCH.sub.3                                                                         O --   CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                0 H  5-N(CH.sub.3).sub. 2                                                                 O --   CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                0 H  H     O --   CH.sub.3                                                                           CH.sub.3 OCH.sub.2 OCH.sub.3                                                                   CH.sub.3                                 0 H  H     O --   CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             N(CH.sub.3).sub.2                        0 H  H     O --   CH.sub.3                                                                           CH.sub.3 CH.sub.3                                                                              CH(OCH.sub.3).sub.2                      0 H  H     O --   CH.sub.3                                                                           CH.sub.3 OC.sub.2 H.sub.5                                                                      CH.sub.3                                 0 H  H     O --   CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             NHCH.sub.3                               0 H  H     O --   CH.sub.3                                                                           CH.sub.3 CH.sub.3                                                                              SCH.sub.3                                0 H  H     O --   CH.sub.3                                                                           CH.sub.3 CH.sub.3                                                                              CCH                                      0 H  H     O --   CH.sub.3                                                                           CH.sub.3 CH.sub.3                                                                              CH.sub.2 SCH.sub.3                       0 H  H     O --   CH.sub.3                                                                           CH.sub.3 CH.sub.3                                                                              SCF.sub.2 H                              0 H  H     O --   CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             N(OCH.sub.3)CH.sub.3                     0 H  H     O --   CH.sub.3                                                                           CH.sub.3 CH.sub.3                                                                              OCH.sub.2 CCH                            0 CH.sub.3                                                                          H     O --   CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                0 H  5-Cl  O --   CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                0 H  5-OCH.sub.3                                                                          O --   CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                0 H  5-SCH.sub.3                                                                          O --   CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                0 H  H     S --   CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                0 H  H     O CH.sub.2                                                                            CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                0 H  H     O --   CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                1 H  H     O --   CH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                1 H  H     O --   CH.sub.3                                                                           CH.sub.3 CH.sub.3                                                                              OCH.sub.3                                1 H  H     O --   CH.sub.3                                                                           CH.sub.3 CH.sub.3                                                                              CH.sub.3                                 1 H  H     O --   CH.sub.3                                                                           CH.sub.3 Cl     OCH.sub.3                                0 H  H     O --   H   CH.sub.2 CH.sub.3                                                                       OCH.sub.3                                                                             OCH.sub.3                                                                               212-215                         0 H  H     O --   H   CH.sub.2 CH.sub.3                                                                       CH.sub.3                                                                              OCH.sub.3                                                                               240-242                         0 H  H     O --   H   CH.sub. 2 CH.sub.3                                                                      CH.sub.3                                                                              CH.sub.3                                 0 H  H     O --   H   (CH.sub.2).sub.3 OCH.sub.3                                                              CH.sub.3                                                                              OCH.sub.3                                                                               136-138                         0 H  H     O --   H   (CH.sub.2).sub.3 OCH.sub.3                                                              OCH.sub.3                                                                             OCH.sub.3                                                                               120-123                         0 H  H     O --   H   (CH.sub.2).sub.3 OCH.sub.3                                                              CH.sub.3                                                                              CH.sub.3                                 __________________________________________________________________________

                                      TABLE V                                      __________________________________________________________________________      ##STR32##                                                                     n R  R.sub.1                                                                              W W.sub.1                                                                           E    R.sub.13                                                                           R.sub.14                                                                           X      Y        m.p. (°C.)                 __________________________________________________________________________     0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                              CH.sub.3                                   0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                             CH.sub.3                                   0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                             OCH.sub.3                                  0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           Cl     OCH.sub.3                                  0 H  H     O O  --   C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           OCH.sub.3                                                                             OCH.sub.3                                  0 H  H     O S  --   CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    OCH.sub.3                                                                             OCH.sub.3                                  0 H  H     O S  --   C.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                                                                    OCH.sub.3                                                                             OCH.sub.3                                                                               165-167                           0 H  H     O S  --   CH.sub.3                                                                            -n-C.sub.4 H.sub.9                                                                OCH.sub.3                                                                             OCH.sub.3                                  0 H  H     O S  --    -n-C.sub.4 H.sub.9                                                                CH.sub.3                                                                           OCH.sub.3                                                                             OCH.sub.3                                  0 H  H     O S  --    .sub.-t-C.sub.4 H.sub.9                                                           CH.sub.3                                                                           OCH.sub.3                                                                             OCH.sub.3                                  0 H  H     O O  --   C.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                                                                    CH.sub.3                                                                              OCH.sub.3                                  0 H  H     O S  --   C.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                                                                    CH.sub.3                                                                              CH.sub.3                                   0 H  5-N(CH.sub.3)                                                                        O S  --   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                             OCH.sub.3                                  0 H  5-Cl  O S  --   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                             OCH.sub.3                                  0 H  5-OCH.sub.3                                                                          O S  --   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                             OCH.sub.3                                  0 H  5-SCH.sub.3                                                                          O S  --   CH.sub. 3                                                                          CH.sub.3                                                                           OCH.sub.3                                                                             OCH.sub.3                                  1 H  H     O O  --   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                             OCH.sub.3                                  0 CH.sub.3                                                                          H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                             OCH.sub.3                                  0 H  H     S S  --   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                             OCH.sub.3                                  0 H  H     O S  CH.sub.2                                                                            CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                             OCH.sub.3                                  0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                              OCH.sub.2 CHCH.sub.2                       0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           OCF.sub.2 H                                                                           CH.sub.3                                   0 H  H     O O  --   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.2 OCH.sub.3                                                                   CH.sub.3                                   0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                             N(CH.sub.3).sub.2                          0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                              CH(OCH.sub.3).sub.2                        0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                      CH.sub.3                                   0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                             NHCH.sub.3                                 0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                              SCH.sub.3                                  0 H  H     O O  --   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                              CCH                                        0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                              CHSCH.sub.3                                0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                              SCF.sub.2 H                                0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                             N(OCH.sub.3)CH.sub.3                       0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                              OCH.sub.2 CCH                              __________________________________________________________________________

                                      TABLE VI                                     __________________________________________________________________________      ##STR33##                                                                     n R  R.sub.1                                                                              W W.sub.1                                                                           E    R.sub.13                                                                           R.sub.14                                                                           X      Y        m.p. (°C.)                 __________________________________________________________________________     0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                              CH.sub.3                                   0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                             CH.sub.3                                   0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                             OCH.sub.3                                  0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           Cl     OCH.sub.3                                  0 H  H     O O  --   C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           OCH.sub.3                                                                             OCH.sub.3                                  0 H  H     O S  --   CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    OCH.sub.3                                                                             OCH.sub.3                                  0 H  H     O S  --   C.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                                                                    OCH.sub.3                                                                             OCH.sub.3                                  0 H  H     O S  --   CH.sub.3                                                                            -n-C.sub.4 H.sub.9                                                                OCH.sub.3                                                                             OCH.sub.3                                  0 H  H     O S  --    -n-C.sub.4 H.sub.9                                                                CH.sub.3                                                                           OCH.sub.3                                                                             OCH.sub.3                                  0 H  H     O S  --    .sub.-t-C.sub.4 H.sub.9                                                           CH.sub.3                                                                           OCH.sub.3                                                                             OCH.sub.3                                  0 H  H     O O  --   C.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                                                                    CH.sub.3                                                                              OCH.sub.3                                  0 H  H     O S  --   C.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                                                                    CH.sub.3                                                                              CH.sub.3                                   0 H  5-N(CH.sub.3)                                                                        O S  --   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                             OCH.sub.3                                  0 H  5-Cl  O S  --   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                             OCH.sub.3                                  0 H  5-OCH.sub.3                                                                          O S  --   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                             OCH.sub.3                                  0 H  5-SCH.sub.3                                                                          O S  --   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                             OCH.sub.3                                  1 H  H     O O  --   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                             OCH.sub.3                                  0 CH.sub.3                                                                          H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                             OCH.sub.3                                  0 H  H     S S  --   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                             OCH.sub.3                                  0 H  H     O S  CH.sub.2                                                                            CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                             OCH.sub.3                                  0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                              OCH.sub.2 CHCH.sub.2                       0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           OCF.sub.2 H                                                                           CH.sub.3                                   0 H  H     O O  --   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.2 OCH.sub.3                                                                   CH.sub.3                                   0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                             N(CH.sub.3).sub.2                          0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                              CH(OCH.sub.3).sub.2                        0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                      CH.sub.3                                   0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                             NHCH.sub.3                                 0 H  H     O S  --   CH.sub. 3                                                                          CH.sub.3                                                                           CH.sub.3                                                                              SCH.sub.3                                  0 H  H     O O  --   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                              CCH                                        0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                              CHSCH.sub.3                                0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                              SCF.sub.2 H                                0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                             N(OCH.sub.3)CH.sub.3                       0 H  H     O S  --   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                              OCH.sub.2 CCH                              __________________________________________________________________________

                                      TABLE VII                                    __________________________________________________________________________      ##STR34##                                                                                  R.sub.13                                                                          or       R.sub.14                                                              R.sub.4                                                        J*                                                                               Q W.sub.1                                                                           R.sub.1                                                                           R.sub.3                                                                           R.sub.15                                                                          or       R.sub.16                                                                          X.sub.1                                                                            Y.sub.1                                                                           m.p.                                        __________________________________________________________________________     1 1 S  H  --    CH.sub.3    CH.sub.3                                                                           O                                              1 1 O  H  --    CH.sub.3    OCH.sub.3                                                                          O                                              1 1 S  5-Cl                                                                              --    C.sub.2 H.sub.5                                                                            OCH.sub.3                                                                          CH.sub.2                                       1 1 S  H  --    CH.sub.2 CHCH.sub.2                                                                        CH.sub.3                                                                           CH                                             1 1 S  H  --    C.sub.6 H.sub.5                                                                            OCH.sub.3                                                                          O                                              1 2 -- H  -- CH.sub.3    CH.sub.3                                                                          OCH.sub.3                                                                          O                                              1 2 -- H  --    (CH.sub.2).sub.4                                                                           OCH.sub.3                                                                          O                                              1 3 S  H  -- CH.sub.3    CH.sub.3                                                                          OCH.sub.3                                                                          O                                              2 1 S  -- --    CH.sub.3    CH.sub.3                                                                           O                                              2 1 S  -- --    CH.sub.3    OCH.sub.3                                                                          O                                              2 1 O  -- --    CH.sub.3    OCH.sub.3                                                                          CH.sub.2                                       2 2 -- -- -- CH.sub.3    CH.sub.3                                                                          OCH.sub.3                                                                          O                                              2 2 -- -- --    (CH.sub.2).sub.4                                                                           OCH.sub.3                                                                          O                                              2 3 S  -- -- CH.sub.3    CH.sub.3                                                                          OCH.sub.3                                                                          O                                              3 1 S  -- --    CH.sub.3    CH.sub.3                                                                           O                                              3 1 S  -- --    CH.sub.3    OCH.sub.3                                                                          O                                              3 1 O  -- --    CH.sub.3    OCH.sub.3                                                                          O                                              3 2 -- -- -- CH.sub.3    CH.sub.3                                                                          OCH.sub.3                                                                          O                                              3 2 -- -- --    (CH.sub.2).sub.4                                                                           OCH.sub.3                                                                          O                                              3 3 S  -- -- CH.sub.3    CH.sub.3                                                                          OCH.sub.3                                                                          O                                              4 1 S  -- --    CH.sub.3    CH.sub.3                                                                           O                                              4 1 S  -- --    CH.sub.3    OCH.sub.3                                                                          O                                              4 1 O  -- --    CH.sub.3    OCH.sub.3                                                                          CH.sub.2                                       4 2 -- -- -- CH.sub.3    CH.sub.3                                                                          OCH.sub.3                                                                          O                                              4 2 -- -- --    (CH.sub.2).sub.4                                                                           OCH.sub.3                                                                          O                                              4 3 S  -- -- CH.sub.3    CH.sub.3                                                                          OCH.sub.3                                                                          O                                              5 1 S  -- H     CH.sub.3    OCH.sub.3                                                                          O                                              5 1 S  -- CH.sub.3                                                                             CH.sub.3    OCH.sub.3                                                                          O                                              5 1 O  -- H     C.sub.2 H.sub.5                                                                            OCH.sub.3                                                                          CH.sub.2                                       5 2 -- -- CH.sub.3                                                                          CH.sub.3    CH.sub.3                                                                          CH.sub.3                                                                           O                                              5 2 -- -- H     (CH.sub.2).sub.4                                                                           OCH.sub.3                                                                          O                                              5 3 S  -- CH.sub.3                                                                          CH.sub.3    CH.sub.3                                                                          OCH.sub.3                                                                          O                                              6 1 S  -- H     CH.sub.3    OCH.sub.3                                                                          O                                              6 1 S  -- CH.sub.3                                                                             CH.sub.3    OCH.sub.3                                                                          O                                              6 1 O  -- H     C.sub.2 H.sub.5                                                                            OCH.sub.3                                                                          CH.sub.2                                       6 2 -- -- CH.sub.3                                                                          CH.sub.3    CH.sub.3                                                                          CH.sub.3                                                                           O                                              6 2 -- -- H     (CH.sub.2).sub.4                                                                           OCH.sub.3                                                                          O                                              6 3 S  -- CH.sub.3                                                                          CH.sub.3    CH.sub.3                                                                          OCH.sub.3                                                                          O                                              7 1 S  -- H     CH.sub.3    OCH.sub.3                                                                          O                                              7 1 S  -- CH.sub.3                                                                             CH.sub.3    OCH.sub.3                                                                          O                                              7 1 O  -- H     C.sub.2 H.sub.5                                                                            OCH.sub.3                                                                          CH.sub.2                                       7 2 -- -- CH.sub.3                                                                          CH.sub.3    CH.sub.3                                                                          CH.sub.3                                                                           O                                              7 2 -- -- H     (CH.sub.2).sub.4                                                                           OCH.sub.3                                                                          O                                              7 3 S  -- CH.sub.3                                                                          CH.sub.3    CH.sub.3                                                                          OCH.sub.3                                                                          O                                              8 1 S  -- H     CH.sub.3    OCH.sub.3                                                                          O                                              8 1 S  -- CH.sub.3                                                                             CH.sub.3    OCH.sub.3                                                                          O                                              8 1 O  -- H     C.sub.2 H.sub.5                                                                            OCH.sub.3                                                                          CH.sub.2                                       8 2 -- -- CH.sub.3                                                                          CH.sub.3    CH.sub.3                                                                          CH.sub.3                                                                           O                                              8 2 -- -- H     (CH.sub.2).sub.4                                                                           OCH.sub.3                                                                          O                                              8 3 S  -- CH.sub.3                                                                          CH.sub.3    CH.sub.3                                                                          OCH.sub.3                                                                          O                                              __________________________________________________________________________      *where J is J1, n = 0, R = H, E = single bond; where J is J2 to J8, n = 0      R.sub.2 = H, R = H.                                                      

                                      TABLE VIII                                   __________________________________________________________________________      ##STR35##                                                                                     R.sub.4                                                        J*                                                                               Q W.sub.1                                                                           R.sub.1                                                                           R.sub.3                                                                           R.sub.15                                                                          or       R.sub.16                                                                          X.sub.1                                                                             Y.sub.1                                                                           m.p.                                       __________________________________________________________________________     1 1 S  H  --    CH.sub.3    OCH.sub.3                                                                           CH.sub.2                                      1 1 O  H  --    CH.sub.3    CH.sub.3                                                                            O                                             1 1 S  5-Cl                                                                              --    C.sub.2 H.sub.5                                                                            OCH.sub.3                                                                           O                                             1 1 S  H  --    CH.sub.2 CHCH.sub.2                                                                        OCF.sub.2 H                                                                         O                                             1 1 S  H  --    C.sub.6 H.sub.5                                                                            OCH.sub.3                                                                           O                                             1 2 -- H  -- CH.sub.3    CH.sub.3                                                                          OC.sub.2 H.sub.5                                                                    O                                             1 2 -- H  --    (CH.sub.2).sub.4                                                                           OCH.sub.3                                                                           O                                             1 3 S  H  -- CH.sub.3    CH.sub.3                                                                          OCH.sub.3                                                                           O                                             2 1 S  -- --    CH.sub.3    OCH.sub.3                                                                           O                                             2 1 S  -- --    CH.sub.3    CH.sub.3                                                                            O                                             2 1 O  -- --    CH.sub.3    OCH.sub.3                                                                           O                                             2 2 -- -- -- CH.sub.3    CH.sub.3                                                                          OC.sub.2 H.sub.5                                                                    O                                             2 2 -- -- --    (CH.sub.2).sub.4                                                                           OCH.sub.3                                                                           O                                             2 3 S  -- -- CH.sub.3    CH.sub.3                                                                          OCH.sub.3                                                                           O                                             3 1 S  -- --    CH.sub.3    OCH.sub.3                                                                           O                                             3 1 S  -- --    CH.sub.3    CH.sub.3                                                                            O                                             3 1 O  -- --    CH.sub.3    OCH.sub.3                                                                           O                                             3 2 -- -- -- CH.sub.3    CH.sub.3                                                                          OC.sub.2 H.sub.5                                                                    O                                             3 2 -- -- --    (CH.sub.2).sub.4                                                                           OCH.sub.3                                                                           O                                             3 3 S  -- -- CH.sub.3    CH.sub.3                                                                          OCH.sub.3                                                                           O                                             4 1 S  -- --    CH.sub.3    OCH.sub.3                                                                           O                                             4 1 S  -- --    CH.sub.3    CH.sub.3                                                                            O                                             4 1 O  -- --    CH.sub.3    OCH.sub.3                                                                           O                                             4 2 -- -- -- CH.sub.3    CH.sub.3                                                                          OC.sub.2 H.sub.5                                                                    O                                             4 2 -- -- --    (CH.sub.2).sub.4                                                                           OCH.sub.3                                                                           O                                             4 3 S  -- -- CH.sub.3    CH.sub.3                                                                          OCH.sub.3                                                                           O                                             5 1 S  -- H     CH.sub.3    OCH.sub.3                                                                           O                                             5 1 S  -- CH.sub.3                                                                             CH.sub.3    CH.sub.3                                                                            O                                             5 1 O  -- H     C.sub.2 H.sub.5                                                                            OC.sub.2 H.sub.5                                                                    O                                             5 2 -- -- CH.sub.3                                                                          CH.sub.3    CH.sub.3                                                                          OCF.sub.2 H                                                                         O                                             5 2 -- -- H     (CH.sub.2).sub.4                                                                           OCH.sub.3                                                                           O                                             5 3 S  -- H  CH.sub.3    CH.sub.3                                                                          OCH.sub.3                                                                           O                                             6 1 S  -- H     CH.sub.3    OCH.sub.3                                                                           O                                             6 1 S  -- CH.sub.3                                                                             CH.sub.3    CH.sub.3                                                                            O                                             6 1 O  -- H     C.sub.2 H.sub.5                                                                            OC.sub.2 H.sub.5                                                                    O                                             6 2 -- -- CH.sub.3                                                                          CH.sub.3    CH.sub.3                                                                          OCF.sub.2 H                                                                         O                                             6 2 -- -- H     (CH.sub.2).sub.4                                                                           OCH.sub.3                                                                           O                                             6 3 S  -- H  CH.sub.3    CH.sub.3                                                                          OCH.sub.3                                                                           O                                             7 1 S  -- H     CH.sub.3    OCH.sub.3                                                                           O                                             7 1 S  -- CH.sub.3                                                                             CH.sub.3    CH.sub.3                                                                            O                                             7 1 O  -- H     C.sub.2 H.sub.5                                                                            OC.sub.2 H.sub.5                                                                    O                                             7 2 -- -- CH.sub.3                                                                          CH.sub.3    CH.sub.3                                                                          OCF.sub.2 H                                                                         O                                             7 2 -- -- H     (CH.sub.2).sub.4                                                                           OCF.sub.2 H                                                                         O                                             7 3 S  -- H  CH.sub.3    CH.sub.3                                                                          OCH.sub.3                                                                           O                                             8 1 S  -- H     CH.sub.3    OCH.sub.3                                                                           O                                             8 1 S  -- CH.sub.3                                                                             CH.sub.3    CH.sub.3                                                                            O                                             8 1 O  -- H     C.sub.2 H.sub.5                                                                            OC.sub.2 H.sub.5                                                                    O                                             8 2 -- -- CH.sub.3                                                                          CH.sub.3    CH.sub.3                                                                          OCF.sub.2 H                                                                         O                                             8 2 -- -- H     (CH.sub.2).sub.4                                                                           OCH.sub.3                                                                           O                                             8 3 S  -- H  CH.sub.3    CH.sub.3                                                                          OCH.sub.3                                                                           O                                             __________________________________________________________________________      *where J is J1, n = 0, R = H, E = single bond; where J is J2 to J8, n = 0      R.sub.2 = H, R = H.                                                      

                                      TABLE IX                                     __________________________________________________________________________      ##STR36##                                                                                     R.sub.4                                                        J*                                                                               Q W.sub.1                                                                           R.sub.1                                                                           R.sub.3                                                                           R.sub.15                                                                          or       R.sub.16                                                                          X.sub.1                                                                             Y.sub.3                                                                           m.p.                                       __________________________________________________________________________     1 1 S  H  --    CH.sub.3    OCH.sub.3                                                                           CH.sub.3                                      1 1 O  H  --    CH.sub.3    OCH.sub.3                                                                           CH.sub.3                                      1 1 S  5-Cl                                                                              --    C.sub.2 H.sub.5                                                                            CH.sub.3                                                                            H                                             1 1 S  H  --    CH.sub.2 CHCH.sub.2                                                                        OCF.sub.2 H                                                                         CH.sub.3                                      1 1 S  H  --    C.sub.6 H.sub.5                                                                            OCH.sub.3                                                                           H                                             1 2 -- H  -- CH.sub.3    CH.sub.3                                                                          OC.sub.2 H.sub.5                                                                    CH.sub.3                                      1 2 -- H  --    (CH.sub.2).sub.4                                                                           OCH.sub.3                                                                           CH.sub.3                                      1 3 S  H  -- CH.sub.3    CH.sub.3                                                                          OCH.sub.3                                                                           CH.sub.3                                      2 1 S  -- --    CH.sub.3    OCH.sub.3                                                                           CH.sub.3                                      2 1 S  -- --    CH.sub.3    CH.sub.3                                                                            H                                             2 1 O  -- --    CH.sub.3    OCH.sub.3                                                                           CH.sub.3                                      2 2 -- -- -- CH.sub.3    CH.sub.3                                                                          OC.sub.2 H.sub.5                                                                    CH.sub.3                                      2 2 -- -- --    (CH.sub.2).sub.4                                                                           OCF.sub.2 H                                                                         H                                             2 3 S  -- -- CH.sub.3    CH.sub.3                                                                          OCH.sub.3                                                                           CH.sub.3                                      3 1 S  -- --    CH.sub.3    OCH.sub.3                                                                           CH.sub.3                                      3 1 S  -- --    CH.sub.3    CH.sub.3                                                                            H                                             3 1 O  -- --    CH.sub.3    OCH.sub.3                                                                           CH.sub.3                                      3 2 -- -- -- CH.sub.3    CH.sub.3                                                                          OC.sub.2 H.sub.5                                                                    CH.sub.3                                      3 2 -- -- --    (CH.sub.2 .sub.4                                                                           OCF.sub.2 H                                                                         H                                             3 3 S  -- -- CH.sub.3    CH.sub.3                                                                          OCH.sub.3                                                                           CH.sub.3                                      4 1 S  -- --    CH.sub.3    OCH.sub.3                                                                           CH.sub.3                                      4 1 S  -- --    CH.sub.3    CH.sub.3                                                                            H                                             4 1 O  -- --    CH.sub.3    OCH.sub.3                                                                           CH.sub.3                                      4 2 -- -- -- CH.sub.3    CH.sub.3                                                                          OC.sub.2 H.sub.5                                                                    CH.sub.3                                      4 2 -- -- --    (CH.sub.2).sub.4                                                                           OCF.sub.2 H                                                                         H                                             4 3 S  -- -- CH.sub.3    CH.sub.3                                                                          OCH.sub.3                                                                           CH.sub.3                                      5 1 S  -- H     CH.sub.3    OCH.sub.3                                                                           CH.sub.3                                      5 1 S  -- CH.sub.3                                                                             CH.sub.3    CH.sub.3                                                                            H                                             5 1 O  -- H     C.sub.2 H.sub.5                                                                            OCH.sub.3                                                                           CH.sub.3                                      5 2 -- -- CH.sub.3                                                                          CH.sub.3    CH.sub.3                                                                          OCF.sub.2 H                                                                         H                                             5 2 -- -- H     (CH.sub.2).sub. 4                                                                          OCH.sub.3                                                                           CH.sub.3                                      5 3 S  -- H  CH.sub.3    CH.sub.3                                                                          OCH.sub.3                                                                           CH.sub.3                                      6 1 S  -- H     CH.sub.3    OCH.sub.3                                                                           CH.sub.3                                      6 1 S  -- CH.sub.3                                                                             CH.sub.3    CH.sub.3                                                                            H                                             6 1 O  -- H     C.sub.2 H.sub.5                                                                            OCH.sub.3                                                                           CH.sub.3                                      6 2 -- -- CH.sub.3                                                                          CH.sub.3    CH.sub.3                                                                          OCF.sub.2 H                                                                         H                                             6 2 -- -- H     (CH.sub.2).sub.4                                                                           OCH.sub.3                                                                           CH.sub.3                                      6 3 S  -- CH.sub.3                                                                          CH.sub.3    CH.sub.3                                                                          OCH.sub.3                                                                           CH.sub.3                                      7 1 S  -- H     CH.sub.3    OCH.sub.3                                                                           CH.sub.3                                      7 1 S  -- CH.sub.3                                                                             CH.sub.3    CH.sub.3                                                                            H                                             7 1 O  -- H     C.sub.2 H.sub.5                                                                            OCH.sub.3                                                                           CH.sub.3                                      7 2 -- -- CH.sub.3                                                                          CH.sub.3    CH.sub.3                                                                          OCF.sub.2 H                                                                         H                                             7 2 -- -- H     (CH.sub.2).sub.4                                                                           OCH.sub.3                                                                           CH.sub.3                                      7 3 S  -- CH.sub.3                                                                          CH.sub.3    CH.sub.3                                                                          OCH.sub.3                                                                           CH.sub.3                                      8 1 S  -- H     CH.sub.3    OCH.sub.3                                                                           CH.sub.3                                      8 1 S  -- CH.sub.3                                                                             CH.sub.3    CH.sub.3                                                                            H                                             8 1 O  -- H     C.sub.2 H.sub.5                                                                            OCH.sub.3                                                                           CH.sub.3                                      8 2 -- -- CH.sub.3                                                                          CH.sub.3    CH.sub.3                                                                          OCF.sub.2 H                                                                         H                                             8 2 -- -- H     (CH.sub.2).sub.4                                                                           OCH.sub.3                                                                           CH.sub.3                                      8 3 S  -- CH.sub.3                                                                          CH.sub.3    CH.sub.3                                                                          OCH.sub.3                                                                           CH.sub.3                                      __________________________________________________________________________      *where J is J1, n = 0, R = H, E = single bond; where J is J2 to J8, n = 0      R.sub.2 = H, R = H.                                                      

                  TABLE X                                                          ______________________________________                                          ##STR37##                                                                                  R.sub.4                                                                        or                                                                J*  Q     W.sub.1                                                                               R.sub.1                                                                             R.sub.3                                                                             R.sub.15                                                                             R.sub.16                                                                             X.sub.2                                                                             Y.sub.2                                                                              m.p.                         ______________________________________                                         1   1     S      H    --   CH.sub.3  CH.sub.3                                                                            OCH.sub.3                            1   1     O      H    --   CH.sub.3  CH.sub.3                                                                            OCH.sub.3                            1   1     S      5-Cl --   C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                     OCF.sub.2 H                          1   1     S      H    --   CH.sub.2 CHCH.sub.2                                                                      CH.sub.3                                                                            SCH.sub.3                            1   1     S      H    --   C.sub.6 H.sub.5                                                                          C.sub.2 H.sub.5                                                                     CH.sub.3                             1   2     --     H    --   CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                            SCF.sub.2 H                        1   2     --     H    --   (CH.sub.2).sub. 4                                                                        CH.sub.3                                                                            OCH.sub.3                            1   3     S      H    --   CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                            OCH.sub.3                          2   1     S      --   --   CH.sub.3  CH.sub.3                                                                            OCH.sub.3                            2   1     S      --   --   CH.sub.3  C.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                     2   1     O      --   --   CH.sub.3  CH.sub.3                                                                            OCH.sub.3                            2   2     --     --   --   CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                            SCH.sub.3                          2   2     --     --   --   (CH.sub.2).sub.4                                                                         CH.sub.3                                                                            OC.sub.2 H.sub.5                     2   3     S      --   --   CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                            OCH.sub.3                          3   1     S      --   --   CH.sub.3  CH.sub.3                                                                            OCH.sub.3                            3   1     S      --   --   CH.sub.3  C.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                     3   1     O      --   --   CH.sub.3  CH.sub.3                                                                            OCH.sub.3                            3   2     --     --   --   CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                            SCH.sub.3                          3   2     --     --   --   (CH.sub.2).sub.4                                                                         CH.sub.3                                                                            OC.sub.2 H.sub.5                     3   3     S      --   --   CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                            OCH.sub.3                          4   1     S      --   --   CH.sub.3  CH.sub.3                                                                            OCH.sub.3                            4   1     S      --   --   CH.sub.3  C.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                     4   1     O      --   --   CH.sub.3  CH.sub.3                                                                            OCH.sub.3                            4   2     --     --   --   CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                            SCH.sub.3                          4   2     --     --   --   (CH.sub.2).sub.4                                                                         CH.sub.3                                                                            OC.sub.2 H.sub.5                     4   3     S      --   --   CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                            OCH.sub.3                          5   1     S      --   H    CH.sub.3  CH.sub.3                                                                            OCH.sub.3                            5   1     S      --   CH.sub.3                                                                            CH.sub.3  C.sub.2 H.sub.5                                                                     OCF.sub.2 H                          5   1     O      --   H    C.sub.2 H.sub.5                                                                          CH.sub.3                                                                            OCH.sub.3                            5   2     --     --   CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                            OC.sub.2 H.sub.5                   5   2     --     --   H    (CH.sub.2).sub.4                                                                         CH.sub.3                                                                            SCH.sub.3                            5   3     S      --   H    CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                            OCH.sub.3                          6   1     S      --   H    CH.sub.3  CH.sub.3                                                                            OCH.sub.3                            6   1     S      --   CH.sub.3                                                                            CH.sub.3  C.sub.2 H.sub.5                                                                     OCF.sub.2 H                          6   1     O      --   H    C.sub.2 H.sub.5                                                                          CH.sub.3                                                                            OCH.sub.3                            6   2     --     --   CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                            OC.sub.2 H.sub.5                   6   2     --     --   H    (CH.sub.2).sub.4                                                                         CH.sub.3                                                                            SCH.sub.3                            6   3     S      --   H    CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                            OCH.sub.3                          7   1     S      --   H    CH.sub.3  CH.sub.3                                                                            OCH.sub.3                            7   1     S      --   CH.sub.3                                                                            CH.sub.3  C.sub.2 H.sub.5                                                                     OCF.sub.2 H                          7   1     O      --   H    C.sub.2 H.sub.5                                                                          CH.sub.3                                                                            OCH.sub.3                            7   2     --     --   CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                            OC.sub.2 H.sub.5                   7   2     --     --   H    (CH.sub.2).sub.4                                                                         CH.sub.3                                                                            SCH.sub.3                            7   3     S      --   H    CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                            OCH.sub.3                          8   1     S      --    H   CH.sub.3  CH.sub.3                                                                            OCH.sub.3                            8   1     S      --   CH.sub.3                                                                            CH.sub.3  C.sub.2 H.sub.5                                                                     OCF.sub.2 H                          8   1     O      --   H    C.sub.2 H.sub.5                                                                          CH.sub.3                                                                            OCH.sub.3                            8   2     --     --   CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                            OC.sub.2 H.sub.5                   8   2     --     --   H    (CH.sub.2).sub.4                                                                         CH.sub.3                                                                            SCH.sub.3                            8   3     S      --   H    CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                            OCH.sub.3                          ______________________________________                                          *where J is J1, n = 0, R = H, E = single bond; where J is J2 to J8, n = 0      R.sub.2 = H, R = H.                                                      

                  TABLE XI                                                         ______________________________________                                          ##STR38##                                                                                   R.sub.4                                                                        or                                                               J*  Q     W.sub.1                                                                               R.sub.1                                                                             R.sub.3                                                                              R.sub.15                                                                             R.sub.16                                                                              X.sub.3                                                                               m.p.                           ______________________________________                                         1   1     S      H    --    CH.sub.3   OCH.sub.3                               1   1     O      H    --    CH.sub.3   OCH.sub.3                               1   1     S      5-Cl --    C.sub.2 H.sub.5                                                                           CH.sub.3                                1   1     S      H    --    CH.sub.2 CHCH.sub.2                                                                       OCH.sub.3                               1   1     S      H    --    C.sub.6 H.sub.5                                                                           CH.sub.3                                1   2     --     H    --    CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                              1   2     --     H    --    (CH.sub.2).sub.4                                                                          OCH.sub.3                               1   3     S      H    --     CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                             2   1     S      --   --    CH.sub.3   CH.sub.3                                2   1     S      --   --    CH.sub.3   OCH.sub.3                               2   1     O      --   --    CH.sub.3   OCH.sub.3                               2   2     --     --   --    CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                              2   2     --     --   --    (CH.sub.2).sub.4                                                                          OCH.sub.3                               2   3     S      --   --    CH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                             3   1     S      --   --    CH.sub.3   CH.sub.3                                3   1     S      --   --    CH.sub.3   OCH.sub.3                               3   1     O      --   --    CH.sub.3   OCH.sub.3                               3   2     --     --   --    CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                              3   2     --     --   --    (CH.sub.2).sub.4                                                                          OCH.sub.3                                3  3     S      --   --    CH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                             4   1     S      --   --    CH.sub.3   CH.sub.3                                4   1     S      --   --    CH.sub.3   OCH.sub.3                               4   1     O      --   --    CH.sub.3   OCH.sub.3                               4   2     --     --   --    CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                              4   2     --     --   --    (CH.sub.2).sub.4                                                                          OCH.sub.3                               4   3     S      --   --    CH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                             5   1     S      --   H     CH.sub.3   CH.sub.3                                5   1     S      --   CH.sub.3                                                                             CH.sub.3   OCH.sub.3                               5   1     O      --   H     C.sub.2 H.sub.5                                                                           OCH.sub.3                               5   2     --     --   CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                              5   2     --     --   H     (CH.sub.2).sub.4                                                                          OCH.sub.3                               5   3     S      --   H     CH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                             6   1     S      --   H     CH.sub.3   CH.sub.3                                6   1     S      --   CH.sub.3                                                                             CH.sub.3   OCH.sub.3                               6   1     O      --   H     C.sub.2 H.sub.5                                                                           OCH.sub.3                               6   2     --     --   CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                              6   2     --     --   H     (CH.sub.2).sub.4                                                                          OCH.sub.3                               6   3     S      --   CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                             7   1     S      --   H     CH.sub.3   CH.sub.3                                7   1     S      --   CH.sub.3                                                                             CH.sub.3   OCH.sub.3                               7   1     O      --   H     C.sub.2 H.sub.5                                                                           OCH.sub.3                               7   2     --     --   CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                              7    2    --     --   H     (CH.sub.2).sub.4                                                                          OCH.sub.3                               7   3     S      --   CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                             8   1     S      --   H     CH.sub.3   CH.sub.3                                8   1     S      --   CH.sub.3                                                                             CH.sub.3   OCH.sub.3                               8   1     O      --   H     C.sub.2 H.sub.5                                                                           OCH.sub.3                               8   2     --     --   CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                              8   2     --     --   H     (CH.sub.2).sub.4                                                                          OCH.sub.3                               8   3     S      --   CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                             ______________________________________                                          *where J is J1, n = 0, R = H, E = single bond; where J is J2 to J8, n = 0      R.sub.2 = H, R = H.                                                      

                                      TABLE XII                                    __________________________________________________________________________      ##STR39##                                                                                    R.sub.4                                                                        or                                                              J*                                                                               Q W.sub.1                                                                           R.sub.1                                                                            R.sub.3                                                                            R.sub.15                                                                           R.sub.16                                                                           X.sub.4                                                                             Y.sub.4                                                                             Z.sub.1                                                                           m.p.                                       __________________________________________________________________________     1 1 S  H   --  CH.sub.3                                                                               CH.sub.3                                                                            CH.sub.3                                                                            CH                                            1 1 O  H   --  CH.sub.3                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                            1 1 S  5-Cl                                                                               --  C.sub.2 H.sub.5                                                                        CH.sub.3                                                                            OCH.sub.3                                                                           N                                             1 1 S  H   --  CH.sub.2 CHCH.sub.2                                                                    OCH.sub.3                                                                           CH.sub.3                                                                            CH                                            1 1 S  H   --  C.sub.6 H.sub.5                                                                        OCH.sub.3                                                                           OCH.sub.3                                                                           N                                             1 2 -- H   --  CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                           Cl   CH                                            1 2 --  H  --  (CH.sub.2).sub.4                                                                       OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                            1 3 S  H   --  CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                            2 1 S  --  --  CH.sub.3                                                                               CH.sub.3                                                                            CH.sub.3                                                                            CH                                            2 1 S  --  --  CH.sub.3                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                           N                                             2 1 O  --  --  CH.sub.3                                                                               OCH.sub.3                                                                           CH.sub.3                                                                            CH                                            2 2 -- --  --  CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                                                                           CH                                            2 2 -- --  --  (CH.sub.2).sub.4                                                                       OCH.sub.3                                                                           Cl   CH                                            2 3 S  --  --  CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                            3 1 S  --  --  CH.sub.3                                                                               CH.sub.3                                                                            CH.sub.3                                                                            CH                                            3 1 S  --  --  CH.sub.3                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                           N                                             3 1 O  --  --  CH.sub.3                                                                               OCH.sub.3                                                                           CH.sub.3                                                                            CH                                            3 2 -- --  --  CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                                                                           CH                                            3 2 -- --  --  (CH.sub.2).sub.4                                                                       CH.sub.3                                                                            Cl   CH                                            3 3 S  --  --  CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                            4 1 S  --  --  CH.sub.3                                                                               CH.sub.3                                                                            CH.sub.3                                                                            CH                                            4 1 S  --  --  CH.sub.3                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                           N                                             4 1 O  --  --  CH.sub.3                                                                               OCH.sub.3                                                                           CH.sub.3                                                                            CH                                            4 2 -- --  --  CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                                                                           CH                                            4 2 -- --  --  (CH.sub. 2).sub.4                                                                      OCH.sub.3                                                                           Cl   CH                                            4 3 S  --  --  CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                            5 1 S  --  H   CH.sub.3                                                                               CH.sub.3                                                                            CH.sub.3                                                                            CH                                            5 1 S  --  CH.sub.3                                                                           CH.sub.3                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                           N                                             5 1 O  --  H   C.sub.2 H.sub.5                                                                        CH.sub.3                                                                            OCH.sub.3                                                                           CH                                            5 2 -- --  CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                           CH.sub.3                                                                            CH                                            5 2 -- --  H   (CH.sub.2).sub.4                                                                       OCH.sub.3                                                                           Cl   CH                                            5 3 S  --  CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                            6 1 S  --  H   CH.sub.3                                                                               CH.sub.3                                                                            CH.sub.3                                                                            CH                                            6 1 S  --  CH.sub.3                                                                           CH.sub.3                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                           N                                             6 1 O  --  H   C.sub.2 H.sub.5                                                                        CH.sub.3                                                                            OCH.sub.3                                                                           CH                                            6 2 -- --  CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                           CH.sub.3                                                                            CH                                            6 2 -- --  H   (CH.sub.2).sub.4                                                                       OCH.sub.3                                                                           Cl   CH                                            6 3 S  --  CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                            7 1 S  --  H   CH.sub.3                                                                               CH.sub.3                                                                            CH.sub.3                                                                            CH                                            7 1 S  --  CH.sub.3                                                                           CH.sub.3                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                           N                                             7 1 O  --  H   C.sub.2 H.sub.5                                                                        CH.sub.3                                                                            OCH.sub.3                                                                           CH                                            7 2 -- --  CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                           CH.sub.3                                                                            CH                                            7 2 -- --  H   (CH.sub.2).sub.4                                                                       OCH.sub.3                                                                           Cl    CH                                           7 3 S  --  CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                            8 1 S  --  H   CH.sub.3                                                                               CH.sub.3                                                                            CH.sub.3                                                                            CH                                            8 1 S  --  CH.sub.3                                                                           CH.sub.3                                                                               OCH.sub.3                                                                           OCH.sub.3                                                                           N                                             8 1 O  --  H   C.sub.2 H.sub.5                                                                        CH.sub.3                                                                            OCH.sub.3                                                                           CH                                            8 2 -- --  CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                           CH.sub.3                                                                            CH                                            8 2 -- --  H   (CH.sub.2).sub.4                                                                       OCH.sub.3                                                                           Cl   CH                                            8 3 S  --  CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                            __________________________________________________________________________      *where J is J1, n = 0, R = H, E = single bond; where J is J2 to J8, n = 0      R.sub.2 = H, R = H.                                                      

                  TABLE XIII                                                       ______________________________________                                          ##STR40##                                                                              R.sub.4                                                                        or                       m.p.                                         J*  Q W.sub.1                                                                              R.sub.3                                                                               R.sub.15                                                                             R.sub.16                                                                             X     Y     Z    (°C.)                   ______________________________________                                         2   1 S     --     CH.sub.3  CH.sub.3                                                                             CH.sub.3                                                                             CH                                    2   1 S     --     CH.sub.3  CH.sub.3                                                                             OCH.sub.3                                                                            CH                                    2   1 S     --     CH.sub.3  OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                    2   1 S     --     CH.sub.3  OCH.sub.3                                                                            Cl    CH                                    2   1 S     --     CH.sub.3  OCH.sub.3                                                                            CH.sub.3                                                                             N                                     2   1 S     --     CH.sub.3  OCH.sub.3                                                                            OCH.sub.3                                                                            N                                     2   1 O     --     CH.sub.3  OCH.sub.3                                                                            CH.sub.3                                                                             CH                                    2   1 O     --     CH.sub.3  OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                    2   1 O     --     CH.sub.3  CH.sub.3                                                                             OCH.sub.3                                                                            N                                     2   2 --    --     CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                            CH                                  2   2 --    --     CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                  2   2 --    --     CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                            CH.sub.3                                                                             N                                   2   2 --    --     CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                            N                                   2   2 --    --     (CH.sub.2).sub.4                                                                         CH.sub.3                                                                             OCH.sub.3                                                                            CH                                    2   2 --    --     (CH.sub.2).sub.4                                                                         OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                    2   2 --    --     (CH.sub.2).sub.4                                                                         CH.sub.3                                                                             OCH.sub.3                                                                            N                                     2   2 --    --     (CH.sub.2).sub.4                                                                         OCH.sub.3                                                                            OCH.sub.3                                                                            N                                     2   3 S     --     CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                  3   1 S     --     CH.sub.3  CH.sub.3                                                                             CH.sub.3                                                                             CH                                    3   1 S     --     CH.sub.3  CH.sub.3                                                                             OCH.sub.3                                                                            CH                                    3   1 S     --     CH.sub. 3 OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                    3   1 S     --     CH.sub.3  OCH.sub.3                                                                            Cl    CH                                    3   1 S     --     CH.sub.3  OCH.sub.3                                                                            CH.sub.3                                                                             N                                     3   1 S     --     CH.sub.3  OCH.sub.3                                                                            OCH.sub.3                                                                            N                                     3   1 O     --     CH.sub.3  OCH.sub.3                                                                            CH.sub.3                                                                             CH                                    3   1 O     --     CH.sub.3  OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                    3   1 O     --     CH.sub.3  CH.sub.3                                                                             OCH.sub.3                                                                            N                                     3   2 S     --     CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                            CH   187-                                                                           188                            3   2 S     --     CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                            CH   193-                                                                           194                            3   2 S     --     CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                            CH.sub.3                                                                             N                                   3   2 S     --     CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                            N    182-                                                                           183                            3   2 S     --     CH.sub.3                                                                             CH.sub.3                                                                             Cl    OCH.sub.3                                                                            CH   183-                                                                           185                            3   2 S     --     (CH.sub.2).sub.4                                                                         CH.sub.3                                                                             OCH.sub.3                                                                            CH                                    3   2 S     --     (CH.sub.2).sub.4                                                                         OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                    3   2 S     --     (CH.sub.2).sub.4                                                                         OCH.sub.3                                                                            CH.sub.3                                                                             N                                     3   2 S     --     (CH.sub.2).sub.4                                                                         OCH.sub.3                                                                            OCH.sub.3                                                                            N                                     3   3 S     --     CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                  4   1 S     --     CH.sub.3  CH.sub.3                                                                             OCH.sub.3                                                                            CH                                    4   1 S     --     CH.sub.3  OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                    4   1 S     --     CH.sub.3  CH.sub.3                                                                             OCH.sub.3                                                                            N                                     4   1 O     --     CH.sub.3  OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                    4   2 --    --     CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                  4   2 --    --     (CH.sub.2).sub.4                                                                         OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                    4   3 S     --     CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                  5   1 S     H      CH.sub.3  CH.sub.3                                                                             OCH.sub.3                                                                            CH                                    5   1 S     CH.sub.3                                                                              CH.sub.3  OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                    5   1 S     H      CH.sub.3  CH.sub.3                                                                             OCH.sub.3                                                                            N                                     5   1 O     H      CH.sub.3  OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                    5   2 --    H      CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                  5   2 --    H      (CH.sub.2).sub.4                                                                         OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                    5   3 S     H      CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                  6   1 S     H      CH.sub.3  CH.sub.3                                                                             OCH.sub.3                                                                            CH                                    6   1 S     CH.sub.3                                                                              CH.sub.3  OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                    6   1 S     H      CH.sub.3  CH.sub.3                                                                             OCH.sub.3                                                                            N                                     6   1 O     H      CH.sub.3  OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                    6   2 --    H      CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                  6   2 --    H      (CH.sub.2).sub.4                                                                         OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                    6   3 S     H      CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                  7   1 S     H      CH.sub.3  CH.sub.3                                                                             OCH.sub.3                                                                            CH                                    7   1 S     CH.sub.3                                                                              CH.sub.3  OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                    7   1 S     H      CH.sub.3  CH.sub.3                                                                             OCH.sub.3                                                                            N                                     7   1 O     H      CH.sub.3  OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                    7   2 --    H      CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                  7   2 --    H      (CH.sub.2).sub.4                                                                         OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                    7   3 S     H      CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                  8   1 S     H      CH.sub.3  CH.sub.3                                                                             OCH.sub.3                                                                            CH                                    8   1 S     CH.sub.3                                                                              CH.sub.3  OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                    8   1 S     H      CH.sub.3  CH.sub.3                                                                             OCH.sub.3                                                                            N                                     8   1 O     H      CH.sub.3  OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                    8   2 --    H      CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                  8   2 --    H      (CH.sub.2).sub.4                                                                         OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                    8   3 S     H      CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                  ______________________________________                                          *n = 0, R = H, R.sub.2 = H.                                              

Formulations

Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 5% to 99.9% solid or liquid diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:

    ______________________________________                                                     Weight Percent                                                                 Active                                                                         Ingredient                                                                             Diluent(s)                                                                               Surfactant(s)                                    ______________________________________                                         Wettable Powders                                                                             20-90      0-74     1-10                                         Oil Suspensions,                                                                              5-50     40-95     0-15                                         Emulsions, Solutions,                                                          (including Emulsifiable                                                        Concentrates)                                                                  Aqueous Suspensions                                                                          10-50     40-84     1-20                                         Dusts          1-25     70-99     0-5                                          Granules and Pellets                                                                          1-95      5-99     0-15                                         High Strength 90-99      0-10     0-2                                          Compositions                                                                   ______________________________________                                    

Lower or higher levels of active ingredients can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, N.J. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0° C. "McCutcheon's Detergents and Emulsifiers Annual", Allured Publ. Corp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth, etc. Preferably, ingredients should be approved by the U.S. Environmental Protection Agency for the use intended.

The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 4th Ed., McGraw-Hill, New York, 1963, pp. 8-59ff.

For further information regarding the art of formulation, see for example:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

EXAMPLE 6

High Strength Concentrate

    ______________________________________                                         2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino-                                                      98.5%                                              sulfonyl]-N,N--dimethylbenzenecarbothioamide                                   silica aerogel              0.5%                                               synthetic amorphous fine silica                                                                            1.0%                                               ______________________________________                                    

The ingredients are blended and ground in a hammermill to produce a high strength concentrate essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). This material may then be formulated in a variety of ways.

EXAMPLE 7

Wettable Powder

    ______________________________________                                         N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(1-                                                        40%                                              pyrrolidinylthioxomethyl)benzenesulfonamide                                    dioctyl sodium sulfosuccinate                                                                               1.5%                                              sodium ligninsulfonate         3%                                              low viscosity methyl cellulose                                                                              1.5%                                              attapulgite                   54%                                              ______________________________________                                    

The ingredients are thoroughly blended, passed through an air mill, to produce an average particle size under 15 microns, reblended, and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) before packaging.

All compounds of the invention may be formulated in the same manner.

EXAMPLE 8

Oil Suspension

    ______________________________________                                         2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino-                                                      35%                                                sulfonyl]-N,N--dimethylbenzenecarbothioamide                                   blend of polyalcohol carboxylic esters                                                                      6%                                                and oil-soluble petroleum sulfonates                                           xylene                      59%                                                ______________________________________                                    

The ingredients are combined and ground together in a sand mill to produce particles essentially all below 3 microns. The product can be used directly, extended with oils, or emulsified in water.

EXAMPLE 9

Extruded Pellet

    ______________________________________                                         N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(1-                                                       25%                                               pyrrolidinylthioxomethyl)benzenesulfonamide                                    anhydrous sodium sulfate     10%                                               crude calcium ligninsulfonate                                                                                5%                                               sodium alkylnaphthalenesulfonate                                                                             1%                                               calcium/magnesium bentonite  59%                                               ______________________________________                                    

The ingredients are blended, hammermilled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.

EXAMPLE 10

High Strength Concentrate

    ______________________________________                                         2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino-                                                      99%                                                sulfonyl]-N,N--dimethylbenzenecarbothioamide                                   trimethylnonyl polyethylene glycol ether                                                                    1%                                                ______________________________________                                    

The surfactant is sprayed upon the active ingredient in a blender and the mixture sifted through a U.S.S. No. 40 sieve (0.42 mm openings) prior to packaging. The concentrate may be formulated further for practical use.

EXAMPLE 11

Granule

    ______________________________________                                         N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(1-                                                       10%                                               pyrrolidinylthioxomethyl)benzenesulfonamide                                    attapulgite granules (low volative matter, 0.71/0.30 mm:                                                    90%                                               U.S.S. No. 25-50 sieves)                                                       ______________________________________                                    

The active ingredient is warmed to approximately 100° C. and sprayed upon dedusted and pre-warmed attapulgite granules in a double-cone blender. The granules are then allowed to cool and are packaged.

EXAMPLE 12

Wettable Powder

    ______________________________________                                         2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino-                                                      50%                                                sulfonyl]-N,N--dimethylbenzenecarbothioamide                                   sodium alkylnaphthalenesulfonate                                                                            2%                                                low viscosity methyl cellulose                                                                              2%                                                diatomaceous earth          46%                                                ______________________________________                                    

The ingredients are blended, coarsely hammermilled and then air milled to produce particles of active essentially all below 10 microns in diameter. The product is reblended before packaging.

EXAMPLE 13

Wettable Powder

    ______________________________________                                         N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(1-                                                       80%                                               pyrrolidinylthioxomethyl)benzenesulfonamide                                    sodium alkylnaphthalenesulfonate                                                                            2%                                                sodium ligninsulfonate       2%                                                synthetic amorphous silica   3%                                                kaolinite                    13%                                               ______________________________________                                    

The ingredients are blended and then ground in a hammermill to produce particles with an average particle size less than 25 microns in diameter. The material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) before being packaged.

EXAMPLE 14

Granule

    ______________________________________                                         wettable powder of Example 13                                                                        15%                                                      gypsum                69%                                                      potassium sulfate     16%                                                      ______________________________________                                    

The ingredients are blended in a rotating mixer and water sprayed on to accomplish granulation. When most of the material has reached the desired range of 1.0 to 0.42 mm (U.S.S. No. 18-40 sieves), the granules are removed, dried, and screened. Oversize material is crushed to produce additional material in the desired range. These granules contain 12% active ingredient.

EXAMPLE 15

Oil Suspension

    ______________________________________                                         2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino-                                                       25%                                               sulfonyl]-N,N--dimethylbenzenecarbothioamide                                   polyoxyethylene sorbitol hexaoleate                                                                          5%                                               highly aliphatic hydrocarbon oil                                                                            70%                                               ______________________________________                                    

The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.

EXAMPLE 16

Aqueous Suspension

    ______________________________________                                         N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(1-                                                      25%                                                pyrrolidinylthioxomethyl)benzenesulfonamide                                    hydrated attapulgite        3%                                                 crude calcium ligninsulfonate                                                                              10%                                                sodium dihydrogen phosphate 0.5%                                               water                       61.5%                                              ______________________________________                                    

The ingredients are ground together in a ball or roller mill until the solid particles have been reduced to diameters under 10 microns.

EXAMPLE 17

Wettable Powder

    ______________________________________                                         2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino-                                                       65%                                               sulfonyl]-N,N--dimethylbenzenecarbothioamide                                   dodecylphenol polyethylene glycol ether                                                                     2%                                                sodium ligninsulfonate       4%                                                sodium silicoaluminate       6%                                                montmorillonite (calcined)   23%                                               ______________________________________                                    

The ingredients are thoroughly blended. The liquid surfactant is added by spraying upon the solid ingredients in the blender. After grinding in a hammermill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.

Utility

Test results indicate that the compounds of the present invention are highly active preemergent or postemergent herbicides or plant growth regulants. many of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, parking lots, drive-in theaters, around billboards, highway and railroad structures. Some of the compounds have utility for selective weed control in crops such as wheat. Alternatively, the subject compounds are useful to modify plant growth.

The rates of application for the compounds of the invention are determined by a number of factors, including their use as plant growth modifiers or as herbicides, the crop species involved, the types of weeds to be controlled, weather and climate, formulations selected, mode of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.01 to 10 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, for plant growth modification or for situations where only short-term persistence is required.

The compounds of the invention may be used in combination with any other commercial herbicide, examples of which are those of the triazine, triazole, uracil, urea, amide, diphenylether, carbamate, and bipyridylium types.

The herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. The test procedures and results follow.

Test A

Seeds of crabgrass (Digitaria sp.), giant foxtail (Setaria faberi), barnyardgrass, (Echinochloa crusgalli), wild oats (Avena fatua), cheatgrass (Bromus secalinus), velvetleaf (Abutilon theophrasti), morningglory (Ipomoea spp.), cocklebur (Xanthium pennsylvanicum), sorghum, corn, soybean, sugarbeet, cotton, rice, wheat, barley and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with the test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were treated with a soil/foliage application. At the same time of treatment, the plants ranged in height from 2 to 18 cm. Treated plants and controls were maintained in a greenhouse for sixteen days, after which all species were compared to controls and visually rated for response to treatment. The ratings, summarized in Table A, are based on a numerical scale extending from 0=no injury, to &=complete kill. The accompanying descriptive symbols have the following meanings:

C=chlorosis or necrosis

B=burn

D=defoliation

E=emergence inhibition

G=growth retardation

H=formative effects

U=unusual pigmentation

X=axillary stimulation

S=albinism

6Y=abscised buds or flowers.

    ______________________________________                                         Compounds                                                                       ##STR41##                                                                     Compound                                                                               R.sub.15  R.sub.16 X      Y      Z                                     ______________________________________                                         1       CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                           OCH.sub.3                                                                               OCH.sub.3                                                                             CH                                      2       CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                           OCH.sub.3                                                                               OCH.sub.3                                                                             N                                       3       CH.sub.3  CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                                                             CH                                    4       CH.sub.3  H        CH.sub.3                                                                              CH.sub.3                                                                              CH                                    5       CH.sub.3  H        CH.sub.3                                                                              OCH.sub.3                                                                             CH                                    6       CH.sub.3  H        OCH.sub.3                                                                             OCH.sub.3                                                                             CH                                    7       CH.sub.3  H        Cl     OCH.sub.3                                                                             CH                                    8       CH.sub.2 CH.sub.3                                                                        H        CH.sub.3                                                                              CH.sub.3                                                                              CH                                    9       CH.sub.2 CH.sub.3                                                                        H        CH.sub.3                                                                              OCH.sub.3                                                                             CH                                    10      CH.sub.2 CH.sub.3                                                                        H        OCH.sub.3                                                                             OCH.sub. 3                                                                            CH                                    11      CH.sub.2 CH.sub.3                                                                        H        Cl     OCH.sub.3                                                                             CH                                    12      CH.sub.2 CH.sub.3                                                                        H        CH.sub.3                                                                              OCH.sub.3                                                                             N                                     13                                                                                      ##STR42##                                                             ______________________________________                                    

                                      TABLE A                                      __________________________________________________________________________                Cmpd. 1                                                                             Cmpd. 2                                                                             Compound 3                                                                             Compound 4                                                                              Compound 5                                                                             Compound 6                                                                              Compound 7              Rate kg/ha 0.05 0.05 0.05                                                                               0.01                                                                               0.05 0.01                                                                               0.05                                                                               0.01                                                                               0.05 0.01                                                                               0.05                                                                               0.01                __________________________________________________________________________     POSTEMERGENCE                                                                  Morningglory                                                                              10C  4C,9G                                                                               10C 2C,8G                                                                              4C,8H                                                                               5H  5C,9G                                                                              3C,8H                                                                              9C   4C,8H                                                                              6C,9G                                                                              2C,5H               Cocklebur  9C   4C,9G                                                                               5C,9G                                                                              2C,7G                                                                              4C,9H                                                                               2C,7H                                                                              4C,9H                                                                              2C,6H                                                                              9H   5G  3C,9H                                                                              4H                  Velvetleaf 9C   4C,5H                                                                               9C  4C,9H                                                                              3C,7H                                                                               1C  4C,9H                                                                              3C,4G                                                                              9C   4C,8H                                                                              3C,4G                                                                              1C                  Nutsedge   9G   3G   6C,9G                                                                              3C,9G                                                                              2C   0   3C,8G                                                                              0   3C,9G                                                                               0   3G  0                   Crabgrass  4G   0    3C,9G                                                                              4G  5G   0   4G  0   1C,3G                                                                               0   0   0                   Giant Foxtail                                                                             --   --   --  --  3C,8H                                                                               2G  3C,8G                                                                               4G 4C,8H                                                                               3C,7H                                                                              2C,5G                                                                              2G                  Barnyardgrass                                                                             5C,9H                                                                               9H   9C  9C  5C,9H                                                                               3H  4C,9H                                                                              3C,7H                                                                              9C   6C,9H                                                                              3C,9H                                                                              7H                  Cheatgrass 8G   3G   3C,9G                                                                              2C,8G                                                                              4C,9G                                                                               4G  4C,9G                                                                              3C,7G                                                                              4C,8G                                                                               3C,8G                                                                              6G  0                   Wild Oats  4C,8G                                                                               0    5C,9G                                                                              3C,9G                                                                              3C,7G                                                                               1C  2C  0   3G   0   0   0                   Wheat      9C   0    4C,9G                                                                              3C,9G                                                                              5G   0   2G  0   5G   0   0   0                   Corn       3U,9H                                                                               2U,9G                                                                               3C,9H                                                                              3C,8H                                                                              1C,5H                                                                               0   2C,6G                                                                              0   2C,5G                                                                               0   0   0                   Barley     --   --   --  --  2C,6G                                                                               0   4G  0   7G   0   0   0                   Soybean    4C,9G                                                                               3C,9G                                                                               4C,9G                                                                              4C,9H                                                                              3C,7H                                                                               3C,3H                                                                              3C,9G                                                                              3C,7G                                                                              6C,9G                                                                               4C,8G                                                                              3C,5H                                                                              2C,2H               Rice       5C,9G                                                                               2C,8G                                                                               9C  5C,9G                                                                              5C,9G                                                                               3C,7G                                                                              9C  3C,7G                                                                              6C,9G                                                                               5C,9G                                                                              6G  3C,7G               Sorghum    3C,9H                                                                               3C,8G                                                                               9C  2C,9H                                                                              4C,9G                                                                               2C,5G                                                                              3C,9H                                                                              3C,5G                                                                              5C,9G                                                                               4C,9H                                                                              4C,9H                                                                              3C,7H               Sugar beet 5C,9G                                                                               3C,8H                                                                               9C  5C,9G                                                                              9C   4C,9G                                                                              9C  4C,9G                                                                              9C   9C  3C,7H                                                                              6H                  Cotton     4C,9G                                                                               4C,8H                                                                               9C  5C,9G                                                                              9C   0   10C 10C 10C  10C 10C 3C,7G               __________________________________________________________________________                Compound 8                                                                             Compound 9                                                                              Compound 10                                                                             Compound 11                                                                             Compound 12                                                                             Compound 13             Rate kg/ha 0.05                                                                               0.01                                                                               0.05 0.01                                                                               0.05 0.01                                                                               0.05 0.01                                                                               0.05 0.01                                                                               0.05                                                                               0.01                __________________________________________________________________________     POSTEMERGENCE                                                                  Morningglory                                                                              3C,8H                                                                              3C,7H                                                                              10C  4C,8G                                                                              4C,9G                                                                               2C,7G                                                                              2C,8G                                                                               3C,6G                                                                              3C,8G                                                                               2C,4H                                                                              2C,4G                                                                              0                   Cocklebur  3C,9H                                                                              3C,6G                                                                              5C,9H                                                                               4C,9H                                                                              3C,9H                                                                               3G  3C,9G                                                                               2C,2H                                                                              3C,9H                                                                               2C,7G                                                                              2C,4G                                                                              0                   Velvetleaf 3C,8H                                                                              3C,8G                                                                              9C   4C,8H                                                                              9C   4C,9G                                                                              2C,8G                                                                               2C,8G                                                                              3C,7H                                                                               2G  1C  0                   Nutsedge   3G  0   3C,9G                                                                               3G  3C,9G                                                                               7G  2G   0   0    0   5G  0                   Crabgrass  0   0   4G   3G  4G   3G  2G   0   0    0   2G  0                   Giant Foxtail                                                                             3G  2G  3C,7G                                                                               3G  2C,8G                                                                               4G  3G   0   2G   0   4G  2G                  Barnyardgrass                                                                             2C,5G                                                                              2H  9C   2C,5H                                                                              9C   3C,7H                                                                              2C,6H                                                                               3H  4H   0   3C,9H                                                                              2C,8H               Cheatgrass 8G  0   9C   7G  5C,9G                                                                               6G  0    0   0    0   9G  5G                  Wild Oats  1C  0   2C,2G                                                                               0   0    0   0    0   0    0   1C  0                   Wheat      0   0   2G   0   0    0   0    0   0    0   2G  0                   Corn       1H  1H  2G   0   3C,6G                                                                               0   0    0   2C,5G                                                                               0   2G  0                   Barley     0   0   2G   0   1C   0   0    0   0    0   3G  0                   Soybean    3C,7H                                                                              0   4C,9G                                                                               3C,8H                                                                              4C,9H                                                                               2C,8H                                                                              4G   2G  2C,7G                                                                               3C,4H                                                                              3C,7H                                                                              2C,2H               Rice       0   0   2C,6G                                                                               0   5C,9G                                                                               2C,8G                                                                              0    0   0    0   0   0                   Sorghum    2C,5G                                                                              2G  2C,7G                                                                               0   9H   7G  2C,8G                                                                               2G  5G   0   3C,8H                                                                              2C                  Sugar beet 3C,8G                                                                              2C,7G                                                                              9C   9C  9C   4C,8G                                                                              3C,7G                                                                               3G  9C   3C,7G                                                                              3C,8H                                                                              2C,5H               Cotton     3C,5G                                                                              2G  10C  7G  9C   3C,8G                                                                              9G   2G  7G   5G  3C,8G                                                                              1C                  __________________________________________________________________________                Cmpd. 1                                                                             Cmpd. 2                                                                             Compound 3                                                                             Compound 4                                                                              Compound 5                                                                             Compound 6                                                                              Compound 7              Rate kg/ha 0.05 0.05 0.05                                                                               0.01                                                                               0.05 0.01                                                                               0.05                                                                               0.01                                                                               0.05 0.01                                                                               0.05                                                                               0.01                __________________________________________________________________________     PREEMERGENCE                                                                   Morningglory                                                                              5H   0    9G  8G  0    0   1C  0   7H   0   0   0                   Cocklebur  2G   0    8H  6G  0    0   2G  --  --   0   0   0                   Velvetleaf 5G   0    5C,9G                                                                              2C,8G                                                                              0    0   8G  3G  6G   4G  0   0                   Nutsedge   4C,8G                                                                               0    10E 3G  0    0   3G  0   5G   0   0   0                   Crabgrass  2C   0    4G  0   0    0   --  0   0    0   0   0                   Giant Foxtail                                                                             --   --   --  --  0    0   0   0   9H   0   0   0                   Barnyardgrass                                                                             3C,7H                                                                               0    3C,9H                                                                              3C,7H                                                                              0    0   0   0   9H   3G  0   0                   Cheatgrass 2C,6G                                                                               0    3C,9G                                                                              6G  0    0   0   0   7G   2G  0   0                   Wild Oats  2C,6G                                                                               0    5C,9G                                                                              3C,6G                                                                              0    0   0   0   1C   0   0   0                   Wheat      3C,7G                                                                               0    3C,9G                                                                              2C,6G                                                                              0    0   3G  0   2G   0   0   0                   Corn       4G   0    9G  2C,3G                                                                              0    0   0   0   3G   0   0   0                   Barley     --   --   --  --  0    0   0   0   2G   0   0   0                   Soybean    0    0    6G  6H  1C   0   1H  0   1C   0   0   0                   Rice       6G   0    10E 8H  0    0   8G  0   9H   3C,8G                                                                              0   0                   Sorghum    2C,3H                                                                               0    9H  4C,8G                                                                              0    0   0   0   4C,8H                                                                               3C,6G                                                                              0   0                   Sugar beet 9G   0    4C,9G                                                                              4C,9G                                                                              0    0   3G  2H  3C,6G                                                                               3H  0   0                   Cotton     0    0    9G  8G  0    0   0   0   5G   0   0   0                   __________________________________________________________________________                Compound 8                                                                             Compound 9                                                                              Compound 10                                                                             Compound 11                                                                             Compound 12                                                                             Compound 13             Rate kg/ha 0.05                                                                               0.01                                                                               0.05 0.01                                                                               0.05 0.01                                                                               0.05 0.01                                                                               0.05 0.01                                                                               0.05                                                                               0.01                __________________________________________________________________________     PREEMERGENCE                                                                   Morningglory                                                                              3G  0   3H   2H  6G   0   4G   0   3G   0   0   0                   Cocklebur  0   4G  2H   0   6G   0   0    0   --   0   0   0                   Velvetleaf --  --  --   --  --   0   8G   --  0    0   0   0                   Nutsedge   0   0   0    0   0    0   0    0   0    0   0   0                   Crabgrass  3G  0   0    0   3G   0   4G   2G  3G   0   0   0                   Giant Foxtail                                                                             3G  0   0    0   4G   2G  4G   2G  2G   0   0   0                   Barnyardgrass                                                                             2G  0   0    0   5G   4G  5G   5G  0    0   0   0                   Cheatgrass 5G  0   0    0   5G   0   0    0   0    0   0   0                   Wild Oats  0   0   0    0   0    0   0    0   0    0   0   0                   Wheat      0   0   0    0   2G   0   0    0   0    0   0   0                   Corn       0   0   2G   0   4G   0   2G   0   2G   0   2G  0                   Barley     0   0   0    0   0    0   3G   0   2G   0   0   0                   Soybean    4G  3G  2C   0   3G   2G  3G   0   7G   0   0   0                   Rice       0   0   0    0   5G   3G  0    0   0    0   0   0                   Sorghum    2G  0   2C   0   4G   2G  4G   0   0    0   0   0                   Sugar beet 3G  0   2C,5G                                                                               0   7G   5G  5G   3G  9G   0   0   0                   Cotton     3G  0   9G   0   5G   0   0    0   0    0   0   0                   __________________________________________________________________________ 

What is claimed is:
 1. A compound of the formula ##STR43## wherein J is ##STR44## W is O or S; R is H or CH₃ ;E is a single bond or --CH₂ --; Q is Q₂ or Q₃ ; Q₂ is ##STR45## Q₃ is ##STR46## n is 0 or 1; W₁ is O or S; R₁ is H, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, Cl, Br, F, NO₂, C₁ -C₃ alkoxy, SO₂ NR_(a) R_(b), C₁ -C₃ alkylthio, C₁ -C₃ alkylsulfinyl, C₁ -C₃ alkylsulfonyl, CN, CO₂ R_(c), C₁ -C₃ haloalkoxy, C₁ -C₃ haloalkylthio, CH₂ OCH₃, CH₂ SCH₃, CH₂ CN, NH₂, NHCH₃ or N(CH₃)₂ ; R₂ is H, Cl, Br, C₁ -C₄ alkyl, C₁ -C₃ alkoxy or C₁ -C₃ alkylthio; R₃ is H, C₁ -C₄ alkyl, C₃ -C₄ alkenyl or phenyl; R_(a) is H, C₁ -C₄ alkyl, C₂ -C₃ cyanoalkyl or C₁ -C₃ alkoxy; R_(b) is H, C₁ -C₄ alkyl or C₃ -C₄ alkenyl; or R_(a) and R_(b) may be taken together as (CH₂)₃, (CH₂)₄, (CH₂)₅ or CH₂ CH₂ OCH₂ CH₂ ; R_(c) is C₁ -C₄ alkyl, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl, C₂ -C₄ haloalkyl, C₂ -C₃ cyanoalkyl, C₅ -C₆ cycloalkyl, C₄ -C₇ cycloalkylalkyl or C₂ -C₄ alkoxyalkyl; R₁₃ is C₁ -C₄ alkyl; R₁₄ is C₁ -C₄ alkyl; R₁₅ is H, C₁ -C₆ alkyl, C₂ -C₃ alkyl substituted with C₁ -C₃ alkoxy or phenoxy, C₃ -C₆ alkenyl, C₃ -C₆ alkynyl, C₃ -C₆ cycloalkyl, C₅ -C₆ cycloalkenyl, C₄ -C₇ cycloalkylalkyl, C₅ -C₆ cycloalkyl substituted with CH₃ or OCH₃, CH₂ CN, CH₂ CH₂ CN, OCH₃, OC₂ H₅, N(CH₃)₂, ##STR47## R₁₆ is H, C₁ -C₆ alkyl, CH₂ CH═CH₂, CH₂ CN or CH₂ CH₂ CN; or R₁₅ and R₁₆ may be taken together to form (CH₂)₃, (CH₂)₄, (CH₂)₅, (CH₂)₆, CH₂ CH═CHCH₂, CH₂ CH₂ OCH₂ CH₂ or CH₂ CH₂ N(CH₃)CH₂ CH₂ ; R₁₇ is H or CH₃ ; R₁₈ is H, C₁ -C₃ alkyl, Cl, Br, OCH₃ or OC₂ H₅ ; R₁₉ is H, C₁ -C₄ alkyl, OCH₃, F, Br, Cl, CF₃, CN, NO₂, SO₂ CH₃, SCH₃ or N(CH₃)₂ ; p is 0 or 1; A is ##STR48## X is H, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄ haloalkyl, C₁ -C₄ haloalkylthio, C₁ -C₄ alkylthio, C₂ -C₅ alkoxyalkoxy, amino, C₁ -C₃ alkylamino or di(C₁ -C₃)alkylamino; Y is H, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄ haloalkylthio, C₁ -C₄ alkylthio, C₂ -C₅ alkoxyalkyl, C₂ -C₅ alkoxyalkoxy, amino, C₁ -C₃ alkylamino, di(C₁ -C₃)alkylamino, C₃ -C₄ alkenyloxy, C₃ -C₄ alkynyloxy, C₂ -C₅ alkylsulfinylalkyl, C₁ -C₄ haloalkyl, C₂ -C₅ alkylsulfonylalkyl, C₃ -C₅ cycloalkyl, C₂ -C₄ alkynyl, C₂ -C₅ alkylthioalkyl, ##STR49## or N(OCH₃)CH₃ W₃ and W₄ are independently O or S; q is 2 or 3; R_(d) is H or CH₃ ; R_(e) is C₁ -C₂ alkyl; R_(f) is C₁ -C₂ alkyl; Z is N;and their agriculturally suitable salts; provided that (a) when W is S, then R is H, and Y is CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃, C₂ H₅, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C CH, OCH₂ CH₂ OCH₃, CH(OCH₃)₂ or ##STR50## (b) X or Y is other than C₁ haloalkoxy; (c) the combined total number of carbon atoms of R₁₅ and R₁₆ is less than or equal to 10; (d) when R₁₅ is CH₂ CN or CH₂ CH₂ CN, then R₁₆ is CH₂ CN or CH₂ CH₂ CN; (e) when R₁₅ is OCH₃ or OC₂ H₅, then R₁₆ is H or CH₃ ; (f) when E is --CH₂ --, then n is 0; and (g) when the total number of carbon atoms of X and Y is greater than four, then the number of carbons of R₁ is less than or equal to two, the number of carbons of R₂ is less than or equal to two, and the number of carbons of Q is less than or equal to four.
 2. Compounds of claim 1 whereW is O; R is H; and R₁₄ is other than C(CH₃)₃.
 3. Compounds of claim 2 whereX is CH₃, OCH₃, OC₂ H₅, CH₂ F, CF₃, OCH₂ CH₂ F, OCH₂ CHF₂, OCH₂ CF₃, CH₂ Cl or CH₂ Br; and Y is H, CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃, NHCH₃, N(OCH₃)CH₃, N(CH₃)₂, C₂ H₅, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, CH₂ OC₂ H₅, OCH₂ CH₂ OCH₃, CH₂ SCH₃, CH₂ SC₂ H₅, cyclopropyl, ##STR51## SCF₂ H, C.tbd.CH or C.tbd.CCH₃.
 4. Compounds of claim 3 whereR₁₅ is H, C₁ -C₃ alkyl, C₃ -C₄ alkenyl or C₃ -C₄ alkynyl; R₁₆ is H, C₁ -C₃ alkyl or CH₂ CH═CH₂ ; or R₁₅ and R₁₆ are taken together to form (CH₂)₄, (CH₂)₅ or CH₂ CH₂ OCH₂ CH₂.
 5. Compounds of claim 4 whereR₂ is H; and R₁ is in the 5-position and selected from H, F, Cl, Br, C₁ -C₂ alkyl, C₁ -C₃ alkoxy or C₁ -C₃ alkylthio.
 6. Compounds of claim 5 whereX is CH₃, OCH₃, OC₂ H₅ or OCH₂ CF₃ ; and Y is CH₃, OCH₃, C₂ H₅, CH₂ OCH₃, NHCH₃ or CH(OCH₃)₂.
 7. Compounds of claim 6 whereR₁ is H, Cl, CH₃ or OCH₃ ; n is O; and E is a single bond.
 8. Compounds of claim 7 whereR₁₃ is C₁ -C₂ alkyl; R₁₄ is C₁ -C₂ alkyl; R₁₅ is H or C₁ -C₃ alkyl; and R₁₆ is H or C₁ -C₃ alkyl.
 9. Compounds of claim 8 where Q is --C(S)NR₁₅ R₁₆.
 10. Compounds of claim 8 where Q is --C(═NR₁₃)W₁ R₁₄.
 11. Compounds of claim 9 where J is J-1.
 12. Compounds of claim 9 where J is J-2.
 13. Compounds of claim 9 where J is J-3.
 14. Comounds of claim 9 where J is J-4.
 15. Compounds of claim 9 where J is J-5.
 16. Compounds of claim 9 where J is J-6.
 17. Compounds of claim 9 where J is J-7.
 18. Compounds of claim 9 where J is J-8.
 19. Compounds of claim 9 where J is J-9.
 20. Compounds of claim 9 where J is J-10.
 21. Compounds of claim 9 where J is J-11.
 22. Compounds of claim 9 where J is J-12.
 23. Compounds of claim 10 where J is J-1.
 24. Compounds of claim 10 where J is J-2.
 25. Compounds of claim 10 where J is J-3.
 26. Compounds of claim 10 where J is J-4.
 27. Compounds of claim 10 where J is J-5.
 28. Compounds of claim 10 where J is J-6.
 29. Compounds of claim 10 where J is J-7.
 30. Compounds of claim 10 where J is J-8.
 31. Compounds of claim 10 where J is J-9.
 32. Compounds of claim 10 where J is J-10.
 33. Compounds of claim 10 where J is J-11.
 34. Compounds of claim 10 where J is J-12.
 35. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of the compound of claim 1 and at least one of the following: surfactant, solid or liquid diluent.
 36. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of the compound of claim 2 and at least one of the following: surfactant, solid or liquid diluent.
 37. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of the compound of claim 3 and at least one of the following: surfactant, solid or liquid diluent.
 38. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of the compound of claim 4 and at least one of the following: surfactant, solid or liquid diluent.
 39. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of the compound of claim 5 and at least one of the following: surfactant, solid or liquid diluent.
 40. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of the compound of claim 6 and at least one of the following: surfactant, solid or liquid diluent.
 41. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of the compound of claim 7 and at least one of the following: surfactant, solid or liquid diluent.
 42. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of the compound of claim 8 and at least one of the following: surfactant, solid or liquid diluent.
 43. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of the compound of claim 9 and at least one of the following: surfactant, solid or liquid diluent.
 44. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of the compound of claim 10 and at least one of the following: surfactant, solid or liquid diluent.
 45. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of the compound of claim 11 and at least one of the following: surfactant, solid or liquid diluent.
 46. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 1. 47. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 2. 48. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 3. 49. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 4. 50. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be prepared an effective amount of a compound of claim
 5. 51. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 6. 52. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 7. 53. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 8,
 54. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 9. 55. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 10. 56. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 11. 